A concise synthesis of (±)-, (+)-, and (-)-6-methyl-6-azabicyclo[3. 2.1]octan-3α-ol

Abraham Philip; J. Bruce Pitner; Young J. Joo; David J. Triggle; F. Ivy Carroll

doi:10.1039/C39900000984

A concise synthesis of (±)-, (+)-, and (-)-6-methyl-6-azabicyclo[3. 2.1]octan-3α-ol

Abraham Philip
, J. Bruce Pitner
, Young J. Joo
, David J. Triggle
, F. Ivy Carroll

School of Pharmacy and Pharmaceutical Sciences

RTI International

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

10 Scopus citations

Abstract

(±)-6-Methyl-6-azabicyclo[3.2.1]octan-3-one (1c) was prepared in three steps from 6-oxabicyclo[3.2.1]oct-3-en-7-one, and stereoselective reduction of (1c) provided (±)-6-methyl-6-azabicyclo[3.2.1]octan- 3α-ol (1a); adaptation of the sequence provided the first synthesis of (+)- and (-)-(1a).

Original language	English
Pages (from-to)	984-985
Number of pages	2
Journal	Journal of the Chemical Society D: Chemical Communications
Issue number	14
DOIs	https://doi.org/10.1039/C39900000984
State	Published - 1990

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title = "A concise synthesis of (±)-, (+)-, and (-)-6-methyl-6-azabicyclo[3. 2.1]octan-3α-ol",

abstract = "(±)-6-Methyl-6-azabicyclo[3.2.1]octan-3-one (1c) was prepared in three steps from 6-oxabicyclo[3.2.1]oct-3-en-7-one, and stereoselective reduction of (1c) provided (±)-6-methyl-6-azabicyclo[3.2.1]octan- 3α-ol (1a); adaptation of the sequence provided the first synthesis of (+)- and (-)-(1a).",

author = "Abraham Philip and Pitner, \{J. Bruce\} and Joo, \{Young J.\} and Triggle, \{David J.\} and Carroll, \{F. Ivy\}",

year = "1990",

doi = "10.1039/C39900000984",

language = "English",

pages = "984--985",

journal = "Journal of the Chemical Society D: Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "14",

}

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T1 - A concise synthesis of (±)-, (+)-, and (-)-6-methyl-6-azabicyclo[3. 2.1]octan-3α-ol

AU - Philip, Abraham

AU - Pitner, J. Bruce

AU - Joo, Young J.

AU - Triggle, David J.

AU - Carroll, F. Ivy

PY - 1990

Y1 - 1990

N2 - (±)-6-Methyl-6-azabicyclo[3.2.1]octan-3-one (1c) was prepared in three steps from 6-oxabicyclo[3.2.1]oct-3-en-7-one, and stereoselective reduction of (1c) provided (±)-6-methyl-6-azabicyclo[3.2.1]octan- 3α-ol (1a); adaptation of the sequence provided the first synthesis of (+)- and (-)-(1a).

AB - (±)-6-Methyl-6-azabicyclo[3.2.1]octan-3-one (1c) was prepared in three steps from 6-oxabicyclo[3.2.1]oct-3-en-7-one, and stereoselective reduction of (1c) provided (±)-6-methyl-6-azabicyclo[3.2.1]octan- 3α-ol (1a); adaptation of the sequence provided the first synthesis of (+)- and (-)-(1a).

UR - https://www.scopus.com/pages/publications/0025162660

U2 - 10.1039/C39900000984

DO - 10.1039/C39900000984

M3 - Article

AN - SCOPUS:0025162660

SN - 0022-4936

SP - 984

EP - 985

JO - Journal of the Chemical Society D: Chemical Communications

JF - Journal of the Chemical Society D: Chemical Communications

IS - 14

ER -

A concise synthesis of (±)-, (+)-, and (-)-6-methyl-6-azabicyclo[3. 2.1]octan-3α-ol

Abstract

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