Sodium triacetoxyborohydride → HCID 57732751, compound

HRID 1806237Notes

Reaction equation

HRID 1806237 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[NH2:32][C@H:33]([CH:36]([CH3:38])[CH3:37])[CH2:34][OH:35].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH:32][C@@H:33]([CH2:34][OH:35])[CH:36]([CH3:38])[CH3:37])[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 6950587D-ValinolHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 57732751HCID 57732751, compoundYield 32.5%

Procedure

Following the general procedure of example 16, 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50 mg, 0.114 mmol), (2R)-2-amino-3-methyl-1-butanol (10.2 mg, 0.087 mmol) and NaBH(OAc)3 (58 mg, 0.261 mmol) were reacted to give the title compound (14.9 mg, 25%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d3b30e08836248d7a9be99abf3e29dcb
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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