Sodium borohydride → HCID 13799992, compound

HRID 475286Notes

Reaction equation

HRID 475286 reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[C:15]([C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[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](=[C:15]([CH:20]([OH:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[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 4311764Sodium borohydrideHCID 71272214HCID 71272214, compound

Product 1

HCID 13799992HCID 13799992, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(1-tosyl-1H-indol-4-yl)ethanone (500 mg, 1.4 mmol, CASRN 112970-73-7) in dry MeOH (5 mL) at 0° C. was added NaBH4 (80 mg, 2.1 mmol) and the mixture was stirred at RT overnight. The mixture was concentrated in vacuo and the residue was diluted with EtOAc, washed sequentially with water and brine. The organics were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 420 mg (95%) of 1-(1-tosyl-1H-indol-4-yl)ethanol (282) as white semi-solid: 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=8.4 Hz, 2H), 7.81-7.76 (m, 2H), 7.37 (d, J=8.0 Hz, 2H), 7.31-7.23 (m, 2H), 6.98 (d, J=3.6 Hz, 1H), 5.23 (d, J=4 Hz, 1H), 5.04-5.01 (m, 1H), 2.30 (s, 3H), 1.33 (d, J=6.4 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted with EtOAc
  3. washwashed sequentially with water and brine
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-6226d9d84931434f84cc1dafc2849e55
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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