tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

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Chemical Name:tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate
CAS No.:1037368-23-2
Molecular Formula:C₂₃H₃₁NO₃
Molecular Weight:369.504
Hs Code.:

Synonyms:tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

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Chemical Property of tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

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Technology Process of tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

There total 2 articles about tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-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: 44.0%

: 1037366-91-8
tert-butyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]-3-(prop-2-en-1-yl)pyrrolidine-3-carboxylate

: 106-95-6
allyl bromide

: 1037368-23-2
tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

: tert-butyl (3S,4S)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -10 ℃; for 0.25h; Inert atmosphere;
DOI:10.3987/COM-18-13889

Reference yield:

: 1037366-91-8
tert-butyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]-3-(prop-2-en-1-yl)pyrrolidine-3-carboxylate

: 106-95-6
allyl bromide

: 1037368-23-2
tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

Reference yield:

: 1037368-23-2
tert-butyl (3S,4R)-5-oxo-1-[(1R)-1-phenylethyl]-3,4-di(prop-2-en-1-yl)pyrrolidine-3-carboxylate

: 1037368-26-5
(3aS,7aR)-3a-amino-2-[(1R)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 15 h / 20 °C

2.2: 0.5 h / 0 - 100 °C / Inert atmosphere

2.3: 6 h / 50 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; trifluoroacetic acid; In dichloromethane; 2.2: |Curtius Rearrangement;
DOI:10.3987/COM-18-13889