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

Base Information

Chemical Name:tert-butyl (3aS,7aS)-1-oxo-2-[(1R)-1-phenylethyl]hexahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate
CAS No.:1037368-61-8
Molecular Formula:C₂₀H₂₇NO₄
Molecular Weight:345.439
Hs Code.:

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

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Chemical Property of tert-butyl (3aS,7aS)-1-oxo-2-[(1R)-1-phenylethyl]hexahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

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Technology Process of tert-butyl (3aS,7aS)-1-oxo-2-[(1R)-1-phenylethyl]hexahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

There total 6 articles about tert-butyl (3aS,7aS)-1-oxo-2-[(1R)-1-phenylethyl]hexahydropyrano[3,4-c]pyrrole-3a(4H)-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: 79.0%

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

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

: 1037368-62-9
tert-butyl (3aS,7aR)-1-oxo-2-[(1R)-1-phenylethyl]hexahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 4h; under 760.051 Torr;
DOI:10.1021/acs.jmedchem.8b00644

Reference yield:

: 915302-93-1
2-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-4-carboxylic acid tert-butyl ester

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

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 18.5 h / 0 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.83 h / -40 - 0 °C / Inert atmosphere

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

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

5.2: 10 h / 40 °C / Inert atmosphere

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

With sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/acs.jmedchem.8b00644

Reference yield:

: C₂₀H₂₅NO₅

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

Guidance literature:: Multi-step reaction with 3 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

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