Sodium hydride → HCID 137329755, compound

HRID 1774745Notes

Reaction equation

HRID 1774745 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:15])([CH3:14])[C@H:8]1[NH:12][C:11](=[O:13])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH2:23]Cl)[CH:22]=1.[H-].[Na+]>>[Br:16][C:17]1[CH:22]=[C:21]([CH2:23][N:12]2[C@H:8]([C:7]([CH3:15])([CH3:14])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9][CH2:10][C:11]2=[O:13])[CH:20]=[N:19][CH:18]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 117012593-Bromo-5-(chloromethyl)pyridineHCID 131731720HCID 131731720, compound

Product 1

HCID 137329755HCID 137329755, compound

Procedure

In analogy to the procedure described for the preparation of intermediates A-12 [B], (S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-one was reacted with 3-bromo-5-chloromethyl-pyridine (intermediate A-12 [A]) in presence of NaH to give the title compound as a colorless oil. MS: 399.2, 401.2 (M+H+).

Sources & evidence

ORD record
ord-1853c59fd60b43fb8603aa79991ac46c
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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