Sodium borohydride → HCID 57894441, compound

HRID 1822162Notes

Reaction equation

HRID 1822162 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:18]([OH:22])[CH:19]([CH3:20])[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57894455HCID 57894455, compound

Product 1

HCID 57894441HCID 57894441, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(1-benzyl-5-chloro-1H-indole-2-yl)-2-methylpropan-1-one (0.6 mmol) in 5 mL of MeOH, was added NaBH4 (1.8 mmol) at 0° C. The mixture was stirred for additional 30 min. The solution was poured into ice water, and extracted with EtOAc (×3). The organic layers were combined, washed with H2O (×3), brine (×3), dried over Na2SO4, filtered, and the filtrate was concentrated to yield 182 mg of 1-(1-benzyl-5-chloro-1H-indole-2-yl)-2-methylpropan-1-ol.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with H2O (×3), brine (×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4a78444e506849c796dc202429aba5bf
Source dataset
uspto-grants-2009_10
Patent number
US07608723B2

Reaction notes

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