Sodium borohydride → HCID 11293992, compound

HRID 599676Notes

Reaction equation

HRID 599676 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:18]=[CH:19][C:20]3[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[S:22][C:21]=3[CH:28]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].[BH4-].[Na+]>C1COCC1>[CH2:13]([C:12]([C:17]1[CH:18]=[CH:19][C:20]2[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[S:22][C:21]=2[CH:28]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:30])[C:2]([CH3:31])([CH3:32])[CH3:1])=[C:7]([CH3:29])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 114651606-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 11293992HCID 11293992, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-2-carboxylic acid (102 mg, 0.226 mmol) in THF (5.0 mL) at RT is treated with NaBH4 (17 mg, 0.451 mmol). The resulting mixture is stirred for 4 h. The reaction is quenched with HCl (1.0 N, 1.0 mL) and extracted with EtOAc (2×20 mL). The organic layer is dried over Na2SO4 and concentrated to afford the title compound (90 mg, 88%).

Workup

  1. customThe reaction is quenched with HCl (1.0 N, 1.0 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-662edce36b4543888aceda2f90a70684
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Reaction notes

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