Sodium borohydride → HCID 9936738, compound

HRID 850678Notes

Reaction equation

[CH:1]12[N:7]([C:8](=[O:39])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=3)=[C:15]4[C@H:29]([CH3:38])[CH2:30][N:31]3[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]3)([CH3:11])[CH3:10])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[BH4-].[Na+]>>[CH:4]12[N:7]([C:8](=[O:39])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([CH3:27])[CH:26]=3)=[C:15]4[C@H:29]([CH3:38])[CH2:30][N:31]3[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]3)([CH3:11])[CH3:10])[CH:1]([CH2:2][CH2:3]1)[CH2:6][CH2:5]2

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 9849748HCID 9849748, compound

Product 1

HCID 9936738HCID 9936738, compoundYield 93%

Procedure

To a solution of (S)-1-{2-[5-[2-(7-aza-bicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-propyl}-piperidin-4-one (15 mg in 0.10 mL dry methanol) at 0° C. was added a solution of sodium borohydride (1 mg in 0.15 mL methanol) and the mixture stirred at low temperature. After 4 hours, the solvent was removed in vacuo and the residue purified by flash chromatography on silica gel (methylene chloride:methanol, 9:1) to give the title compound (14 mg).

Workup

customthe solvent was removed in vacuo
customthe residue purified by flash chromatography on silica gel (methylene chloride:methanol, 9:1)

Sources & evidence

ORD record: ord-c0ab6958b1f946f2a752f7ab33d97dd2
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017944

Reaction notes

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