(1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate

Base Information

Chemical Name:(1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate
CAS No.:1269425-79-7
Molecular Formula:C₁₈H₂₅NO₅S
Molecular Weight:367.466
Hs Code.:

Synonyms:(1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate

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Chemical Property of (1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate

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Technology Process of (1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate

There total 4 articles about (1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-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: 61.0%

: 1269425-69-5
(2S)-tert-butyl 5-hydroxy-1-tosylpyrrolidine-2-carboxylate

: diphenyl(vinyl)sulfonium trifluoromethanesulfonate

: 1269425-79-7
(1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate

Guidance literature:: (2S)-tert-butyl 5-hydroxy-1-tosylpyrrolidine-2-carboxylate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h; Inert atmosphere;

diphenyl(vinyl)sulfonium trifluoromethanesulfonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 15h; optical yield given as %ee; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/asia.201000817

Reference yield:

: 463962-06-3
tert-butyl (2S)-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinecarboxylate

: 1269425-79-7
(1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

2.2: 15 h / 0 - 20 °C / Inert atmosphere

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/asia.201000817

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 1269425-79-7
(1R,4S,7S)-tert-butyl 3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: perchloric acid / 12 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

4.2: 15 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; perchloric acid; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1002/asia.201000817