1-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehyde → (1-tosyl-1H-indol-3-yl)methanol

HRID 41534

Reaction equation

HRID 41534 reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=[O:21])=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[BH4-].[Na+]>CO>[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][OH:21])=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 839263(1-tosyl-1H-indol-3-yl)methanolYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-tosyl-1H-indole-3-carbaldehyde (7 g, 23.385 mmol) in MeOH (70 mL), NaBH4 (1.77 g, 46.769 mmol) was added at 0° C. and the mixture was stirred for 10 min. The reaction mixture was allowed to warm to rt and stirring was continued for 18 h. The solvent was removed under reduced pressure at 45° C. and the crude reaction mixture was quenched with saturated aqueous ammonium chloride solution. Ethyl acetate was added and the organic layer was washed with water and brine. The organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to yield a solid (6.5 g, 92%). [1H-NMR (CDCl3, 300 MHz) δ 8.02-7.95 (m, 1H), 7.82-7.75 (m, 2H), 7.65-7.53 (m, 2H), 7.40-7.19 (m, 4H)].

Workup

  1. stirringstirring
  2. waitwas continued for 18 h
  3. customThe solvent was removed under reduced pressure at 45° C.
  4. customthe crude reaction mixture
  5. customwas quenched with saturated aqueous ammonium chloride solution
  6. additionEthyl acetate was added
  7. washthe organic layer was washed with water and brine
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13947a147af8496a8baa8ac63ebdbe9e
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Linked notes

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