Sodium hydride → HCID 86679124, compound

HRID 1774744Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1)=[O:4].[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH2:17]Cl)[CH:16]=1.[H-].[Na+]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:17][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([Br:10])[CH:16]=1)=[O:4]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 853477Methyl L-prolinate

HCID 117012593-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 86679124HCID 86679124, compound

Procedure

In analogy to the procedure described for the preparation of intermediates A-12 [B], (S)-pyrrolidine-2-carboxylic acid methyl ester was reacted with 3-bromo-5-chloromethyl-pyridine (intermediate A-12 [A]) in presence of NaH to give the title compound as a light yellow oil. MS: 299.2, 301.1 (M+H+).

Sources & evidence

ORD record: ord-f3843147e574491794a6d175c1d71021
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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