2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate

Base Information

Chemical Name:2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate
CAS No.:1037368-63-0
Molecular Formula:C₂₀H₂₇NO₅
Molecular Weight:361.438
Hs Code.:

Synonyms:2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate

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Chemical Property of 2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate

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Technology Process of 2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate

There total 5 articles about 2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate 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: 68.0%

: 1037368-61-8
tert-butyl (3aS,7aS)-1-oxo-2-[(1R)-1-phenylethyl]hexahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

: 501-53-1,94274-21-2
benzyl chloroformate

: 1037368-63-0
2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate

Guidance literature:: tert-butyl (3aS,7aS)-1-oxo-2-[(1R)-1-phenylethyl]hexahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate; With borane-THF; In tetrahydrofuran; at 20 ℃; for 72h; Inert atmosphere;

With triethylamine; In tetrahydrofuran; ethanol; water; at 80 ℃; for 2h; Inert atmosphere;

benzyl chloroformate; In 1,2-dichloro-ethane; at 40 ℃; for 24h;
DOI:10.1021/acs.jmedchem.8b00644

Reference yield:

: C₂₀H₂₅NO₅

: 1037368-63-0
2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / water; tetrahydrofuran; ethyl acetate / 10 h / 20 °C / Inert atmosphere

2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.5 h / -10 °C / Inert atmosphere

2.2: 10 h / 40 °C / Inert atmosphere

3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / 38002.6 Torr

4.1: borane-THF / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

4.2: 2 h / 80 °C / Inert atmosphere

4.3: 24 h / 40 °C

With sodium tetrahydroborate; borane-THF; palladium 10% on activated carbon; hydrogen; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate;
DOI:10.1021/acs.jmedchem.8b00644

Reference yield:

: 1037368-60-7
tert-butyl (3aS)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,6-tetrahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

: 1037368-63-0
2-benzyl 3a-tert-butyl (3aS,7aS)-tetrahydropyrano[3,4-c]pyrrole-2,3a(3H,4H)-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / 38002.6 Torr

2.1: borane-THF / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

2.2: 2 h / 80 °C / Inert atmosphere

2.3: 24 h / 40 °C

With borane-THF; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/acs.jmedchem.8b00644