Sodium borohydride → (3-(Hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

HRID 630453Notes

Reaction equation

HRID 630453 reaction equation
[BH4-].[Na+].[N:3]1([C:9]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH:20]=[O:21])=[CH:16][NH:17]3)=[CH:13][CH:12]=2)=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1>CO>[OH:21][CH2:20][C:15]1[C:14]2[C:18](=[CH:19][C:11]([C:9]([N:3]3[CH2:8][CH2:7][O:6][CH2:5][CH2:4]3)=[O:10])=[CH:12][CH:13]=2)[NH:17][CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1186660826-(Morpholine-4-carbonyl)-1H-indole-3-carbaldehyde

Product 1

HCID 118666232(3-(Hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (220 mg, 5.81 mmol, 3.0 eq) was added to a stirred solution of product 27a) (500 mg, 1.94 mmol, 1.0 eq) in methanol (10 mL) at room temperature and stirring was continued for 2 h. The methanol was removed under vacuum, water (50 mL) was added, and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, and evaporated. White solid. Yield: 400 mg (80% of theory).

Workup

  1. customThe methanol was removed under vacuum, water (50 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-05e2c5a0baa74ce59d97e6a7e4a46d23
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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