Sodium borohydride → HCID 67250021, compound

HRID 41600Notes

Reaction equation

HRID 41600 reaction equation
[CH3:1][C:2]1[N:3]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[BH4-].[Na+]>CO>[CH3:1][C:2]1[N:3]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=2)(=[O:14])=[O:15])[C:4]2[C:9]([C:10]=1[CH2:11][OH:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13586394HCID 13586394, compound

Product 1

HCID 67250021HCID 67250021, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-methyl-1-tosyl-1H-indole-3-carbaldehyde [104142-15-6] (1.2 g, 3.83 mmol) in methanol (40 mL), NaBH4 (145 mg, 3.83 mmol) was added at 0° C. and stirred for 10 min. Then the mixture was allowed to warm to rt and stirred for 4 h. The mixture was concentrated under reduced pressure at 45° C., saturated aqueous NH4Cl solution was added and extracted with ethyl acetate (2×). The combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. The organic layer was filtered and concentrated under reduced pressure to yield the title compound as a pale yellow liquid (1.0 g, 83%). [TLC Rf=0.16 (ethyl acetate/hexane 30:70)].

Workup

  1. stirringstirred for 4 h
  2. concentrationThe mixture was concentrated under reduced pressure at 45° C.
  3. additionsaturated aqueous NH4Cl solution was added
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationThe organic layer was filtered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-469dc05b96b24b0493a6a2168413ee21
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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