Sodium borohydride → 6-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-benzo[b]thiophene-2-carboxylic acid dimethylamide

HRID 730962Notes

Reaction equation

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

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 11465756HCID 11465756, compound

Product 1

HCID 114430486-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-benzo[b]thiophene-2-carboxylic acid dimethylamideYield 100%

Procedure

6-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-2-carboxylic acid dimethylamide (235 mg, 0.490 mmol) is reduced by NaBH4 (37 mg, 0.980 mmol) as in Step F11 to afford the title compound (230 mg, 100%).

Sources & evidence

ORD record: ord-9061d8508d894c7183ad698d17d386c2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582775B2

Reaction notes

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