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

HRID 630508Notes

Reaction equation

HRID 630508 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 (2.2 g, 58.34 mmol) was added at 0° C. portion wise to a suspension of 6-(morpholine-4-carbonyl)-1H-indole-3-carbaldehyde (5 g, 19.44 mmol) in methanol (106 mL) and the mixture was stirred at room temperature for 3 h. The methanol was removed under vacuum whereby the temperature was kept below <35° C. The residue was diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate and evaporated. Washing of the remnant with ether provided the product as white solid. Yield: 4 g (79% of theory)

Workup

  1. customThe methanol was removed under vacuum whereby the temperature
  2. customwas kept below <35° C
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. washWashing of the remnant with ether

Sources & evidence

ORD record
ord-ef67e4a6008a481f9781bd39db30a49c
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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