(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

Base Information

Chemical Name:(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate
CAS No.:1339021-78-1
Molecular Formula:C₁₆H₁₈N₂O₃
Molecular Weight:286.331
Hs Code.:

Synonyms:(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

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Chemical Property of (S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

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Technology Process of (S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

There total 9 articles about (S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-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: 61.0%

: 1339021-68-9
(S)-7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carbonyl azide

: 100-51-6,185532-71-2
benzyl alcohol

: 1339021-78-1
(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

Guidance literature:: In toluene; at 80 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol202381m

Reference yield:

: 851028-60-9
(S)-tert-butyl 2-formyl-2-methylpyrrolidine-1-carboxylate

: 1339021-78-1
(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 3.33 h / -78 °C

2.1: Dess-Martin periodane / dichloromethane / 18 h / 0 - 20 °C

2.2: 0.25 h

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -30 - 0 °C

4.1: potassium hydroxide / water; acetonitrile / 2 h

5.1: diphenylphosphoranyl azide / N,N-dimethyl-formamide / 3 h / 0 °C

6.1: toluene / 1 h / 80 °C / Inert atmosphere

With n-butyllithium; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; Dess-Martin periodane; potassium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Dess-Martin oxidation / 6.1: Curtius rearrangement;
DOI:10.1021/ol202381m

Reference yield:

: 1339022-12-6
(S)-tert-butyl 2-[1-hydroxy-4-methoxy-4-oxobut-2-ynyl]-2-methylpyrrolidine-1-carboxylate

: 1339021-78-1
(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Dess-Martin periodane / dichloromethane / 18 h / 0 - 20 °C

1.2: 0.25 h

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -30 - 0 °C

3.1: potassium hydroxide / water; acetonitrile / 2 h

4.1: diphenylphosphoranyl azide / N,N-dimethyl-formamide / 3 h / 0 °C

5.1: toluene / 1 h / 80 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; Dess-Martin periodane; potassium hydroxide; In dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Dess-Martin oxidation / 5.1: Curtius rearrangement;
DOI:10.1021/ol202381m