Water → N-(4-fluoro-benzyl)-4-[3-(3-hydroxy-cyclopentyl)-indole-1-sulfonyl]-benzamide

HRID 737030Notes

Reaction equation

HRID 737030 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:37]=[CH:36][C:7]([CH2:8][NH:9][C:10](=[O:35])[C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]([CH:29]4[CH2:33][CH2:32][C:31](=[O:34])[CH2:30]4)=[CH:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.O>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10](=[O:35])[C:11]2[CH:12]=[CH:13][C:14]([S:17]([N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]([CH:29]4[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30]4)=[CH:21]3)(=[O:18])=[O:19])=[CH:15][CH:16]=2)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58975183N-(4-Fluoro-benzyl)-4-[3-(3-oxo-cyclopentyl)-indole-1-sulfonyl]-benzamide

Product 1

HCID 58975208N-(4-fluoro-benzyl)-4-[3-(3-hydroxy-cyclopentyl)-indole-1-sulfonyl]-benzamideYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Add sodium borohydride (23 mg, 0.601 mmol) to a 0° C. solution of N-(4-fluoro-benzyl)-4-[3-(3-oxo-cyclopentyl)-indole-1-sulfonyl]-benzamide (295 mg, 0.601 mmol) in MeOH (7 ml) under N2. Stir for 30 min and them warm to room temperature. Stir for 18 hours. Add a small amount of water to quench reaction and then remove MeOH on rotovap. Add EtOAc and water and extract the product into organics. Separate, and dry organics over MgSO4. Condense organics on rotovap and then purify by silica gel chromatography to give N-(4-fluoro-benzyl)-4-[3-(3-hydroxy-cyclopentyl)-indole-1-sulfonyl]-benzamide (205 mg, 69% yield) as a light orange solid. Mass Spectrum (m/e): 493.01 (MH+).

Workup

  1. stirringStir for 18 hours
  2. customto quench
  3. customreaction
  4. extractionAdd EtOAc and water and extract the product into organics
  5. customSeparate
  6. customCondense organics on rotovap
  7. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-2538b49b20f44a789313fba4f64a4bf7
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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