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

Base Information

Chemical Name:tert-butyl (3aS)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,6-tetrahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate
CAS No.:1037368-60-7
Molecular Formula:C₂₀H₂₅NO₄
Molecular Weight:343.423
Hs Code.:

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

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Chemical Property of tert-butyl (3aS)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,6-tetrahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

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Technology Process of tert-butyl (3aS)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,6-tetrahydropyrano[3,4-c]pyrrole-3a(4H)-carboxylate

There total 5 articles about tert-butyl (3aS)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,6-tetrahydropyrano[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:

: 1037368-59-4
tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate

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

Guidance literature:: tert-butyl (3S)-3-[(2-ethoxy-2-oxoethoxy)methyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1.5h;

With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 1h;

With water; ammonium chloride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; more than 3 stages;

Reference yield:

: C₂₀H₂₇NO₅

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

Guidance literature:: C₂₀H₂₇NO₅; With methanesulfonyl chloride; triethylamine; In dichloromethane; at -10 ℃; for 0.5h; Inert atmosphere;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 40 ℃; for 10h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.8b00644

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With sodium tetrahydroborate; 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