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

HRID 420055Notes

Reaction equation

HRID 420055 reaction equation
[CH2:1]([N:8]([CH3:24])[C:9]([C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]1C(OC(C)(C)C)=O)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].C(N(C)C([C@@H]1C[C@@H](O)CN1)=O)CCCC=C>>[CH2:1]([N:8]([CH3:24])[C:9]([C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][NH:12]1)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

3

Reactant 2

HCID 57816715(2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamideHCID 66650539(2S,4R)-tert-butyl 2-(N-(hept-6-enyl)-N-methylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 66650663(2S,4R)-2-N-(hept-6-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamideYield 35%

Procedure

Compound 71a was synthesized from compound 70a as yellow oil in 35% yield, following the procedure as described for compound 49.

Sources & evidence

ORD record
ord-1c08eb904c2342ae8b4b903799e1bc96
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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