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

Base Information

Chemical Name:tert-butyl (1S,5R)-1-(phenylcarbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate
CAS No.:1435903-28-8
Molecular Formula:C₁₇H₂₂N₂O₃
Molecular Weight:302.373
Hs Code.:

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

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

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

There total 7 articles about tert-butyl (1S,5R)-1-(phenylcarbamoyl)-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: 67.0%

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

: 103-71-9
phenyl isocyanate

: 1435903-28-8
tert-butyl (1S,5R)-1-(phenylcarbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: tert-butyl (1R,5R)-1-(p-tolylsulfinyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; at 20 ℃; for 0.0166667h; Inert atmosphere;

phenyl isocyanate; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere;
DOI:10.1021/ja4033956

Reference yield:

: 103-71-9
phenyl isocyanate

: tert-butyl 4-chloropiperidine-1-carboxylate

: 1435903-28-8
tert-butyl (1S,5R)-1-(phenylcarbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

: 1435903-30-2
tert-butyl (1R,5S)-1-(phenylcarbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

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

phenyl isocyanate; In diethyl ether; hexane; at 20 ℃; for 18h; Overall yield = 94 %; Overall yield = 283 mg; Inert atmosphere;
DOI:10.1021/ja4033956

Reference yield:

: 109384-19-2
t-butyl 4-hydroxy piperidine-1-carboxylate

: 1435903-28-8
tert-butyl (1S,5R)-1-(phenylcarbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hexachloroethane; triphenylphosphine / dichloromethane / 16 h / 20 °C / Inert atmosphere

2.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / diethyl ether; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

3.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0.02 h / 20 °C / Inert atmosphere

3.2: 0.08 h / 20 °C / Inert atmosphere

With N,N,N,N,-tetramethylethylenediamine; hexachloroethane; sec.-butyllithium; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja4033956