tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Base Information

Chemical Name:tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate
CAS No.:1435903-11-9
Molecular Formula:C₁₇H₂₃NO₃S
Molecular Weight:321.441
Hs Code.:

Synonyms:tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

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Chemical Property of tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

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Technology Process of tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

There total 6 articles about tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 26.0%

: 1517-82-4
(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

: tert-butyl 4-chloropiperidine-1-carboxylate

: tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

: 1435903-11-9
tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

: 1435903-12-0
tert-butyl (1S,5S)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: tert-butyl 4-chloropiperidine-1-carboxylate; With sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In diethyl ether; hexane; at -78 ℃; for 1h; Inert atmosphere;

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 0.0833333h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja4033956

Reference yield:

: 1517-82-4
(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

: tert-butyl 4-chloropiperidine-1-carboxylate

: tert-butyl (1S,5S)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

: tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

: 1435903-11-9
tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

: 1435903-12-0
tert-butyl (1S,5S)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: tert-butyl 4-chloropiperidine-1-carboxylate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; hexane; at -78 ℃; for 1h; Inert atmosphere;

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1021/ja4033956

Reference yield:

: 824-79-3
sodium 4-methylbenzenesulfinate

: 1435903-11-9
tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

: 1435903-12-0
tert-butyl (1S,5S)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: thionyl chloride / toluene / 2 h / 0 - 20 °C

2.1: pyridine / diethyl ether / 16 h / 0 - 20 °C

3.1: sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine / diethyl ether; hexane / 1 h / -78 °C / Inert atmosphere

3.2: 0.08 h / -78 °C / Inert atmosphere

With pyridine; thionyl chloride; sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In diethyl ether; hexane; toluene;
DOI:10.1021/ja4033956