tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate

Base Information

Chemical Name:tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate
CAS No.:254909-23-4
Molecular Formula:C₁₇H₂₂N₂O₄
Molecular Weight:318.373
Hs Code.:

Synonyms:tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate

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Chemical Property of tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate

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Technology Process of tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate

There total 5 articles about tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate 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: 46.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 103201-79-2,1820583-17-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 254909-23-4
tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate

Guidance literature:: (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

With diphenyl phosphoryl azide; In tetrahydrofuran; for 0.0833333h;

di-tert-butyl dicarbonate; In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1039/b503994k

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 254909-23-4
tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / toluene / 23 h / Reflux; Dean-Stark

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

2.2: 0.17 h

2.3: 17 h

With toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; toluene;

Reference yield:

: 103201-79-2,1820583-17-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 254909-23-4
tert-butyl N-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]oxazol-6-yl]carbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: (PhO)2P(O)N₃ / tetrahydrofuran

2.1: tetrahydrofuran / -78 - 0 °C

With lithium diisopropyl amide; In tetrahydrofuran; 1.1: Metallation / 1.2: Substitution / 2.1: Acylation;
DOI:10.1039/a906297a