(2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide → (2S,4R)-2-N-(oct-6-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide

Reaction equation

[CH2:1]([N:9]([CH3:25])[C:10]([C@@H:12]1[CH2:16][C@@H:15]([OH:17])[CH2:14][N:13]1C(OC(C)(C)C)=O)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH3:8].C(N(C)C([C@@H]1C[C@@H](O)CN1)=O)CCCC=C>>[CH2:1]([N:9]([CH3:25])[C:10]([C@@H:12]1[CH2:16][C@@H:15]([OH:17])[CH2:14][NH:13]1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH3:8]

Participants

Reactant 2

HCID 57816715(2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide

HCID 66650516(2S,4R)-tert-butyl 2-(N-(oct-6-enyl)-N-methylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 66650732(2S,4R)-2-N-(oct-6-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamideYield 51%

Procedure

Compound 71b was synthesized from compound 70b as yellow oil in 51% yield, following the procedure as described for compound 49.

Sources & evidence

ORD record: ord-cb382071a55247b2bfe5df5cfe827181
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093379B2

Reaction notes

Loading…