The reductive cleavage of cyclic aminol ethers to N,N-dialkylaminoderivatives: Modifications to the Eschweiler-Clarke procedure

Philip C. Bulman Page; Harry Heaney; Gerasimos A. Rassias; Serge Reignier; Edward P. Sampler; Salem Talib

doi:10.1055/s-2000-6459

The reductive cleavage of cyclic aminol ethers to N,N-dialkylaminoderivatives: Modifications to the Eschweiler-Clarke procedure

Philip C. Bulman Page, Harry Heaney, Gerasimos A. Rassias, Serge Reignier, Edward P. Sampler, Salem Talib

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

Abstract

The reductive cleavage of cyclic aminol ethers to give N-alkylamino- derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.

Original language	English
Pages (from-to)	104-106
Number of pages	3
Journal	Synlett
Volume	2000
Issue number	1
DOIs	https://doi.org/10.1055/s-2000-6459
Publication status	Published - 2000

Keywords

ring opening
chlorotrimethylsilane
SECONDARY
1
sodium cyanoborohydride
ASYMMETRIC-SYNTHESIS
reductive
3-OXAZOLIDINES
chiral heterocycles
aminol ethers

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10.1055/s-2000-6459

Cite this

@article{ce574ac42f9948f58a3da3cfec9dcf11,

title = "The reductive cleavage of cyclic aminol ethers to N,N-dialkylaminoderivatives: Modifications to the Eschweiler-Clarke procedure",

abstract = "The reductive cleavage of cyclic aminol ethers to give N-alkylamino- derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.",

keywords = "ring opening, chlorotrimethylsilane, SECONDARY, 1, sodium cyanoborohydride, ASYMMETRIC-SYNTHESIS, reductive, 3-OXAZOLIDINES, chiral heterocycles, aminol ethers",

author = "{Bulman Page}, {Philip C.} and Harry Heaney and Rassias, {Gerasimos A.} and Serge Reignier and Sampler, {Edward P.} and Salem Talib",

year = "2000",

doi = "10.1055/s-2000-6459",

language = "English",

volume = "2000",

pages = "104--106",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - The reductive cleavage of cyclic aminol ethers to N,N-dialkylaminoderivatives: Modifications to the Eschweiler-Clarke procedure

AU - Bulman Page, Philip C.

AU - Heaney, Harry

AU - Rassias, Gerasimos A.

AU - Reignier, Serge

AU - Sampler, Edward P.

AU - Talib, Salem

PY - 2000

Y1 - 2000

N2 - The reductive cleavage of cyclic aminol ethers to give N-alkylamino- derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.

AB - The reductive cleavage of cyclic aminol ethers to give N-alkylamino- derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.

KW - ring opening

KW - chlorotrimethylsilane

KW - SECONDARY

KW - 1

KW - sodium cyanoborohydride

KW - ASYMMETRIC-SYNTHESIS

KW - reductive

KW - 3-OXAZOLIDINES

KW - chiral heterocycles

KW - aminol ethers

U2 - 10.1055/s-2000-6459

DO - 10.1055/s-2000-6459

M3 - Article

VL - 2000

SP - 104

EP - 106

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 1

ER -