6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one → HCID 597396, compound

HRID 898346Notes

Reaction equation

HRID 898346 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([OH:15])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 7085296-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 597396HCID 597396, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (500 mg, 1.9 mmol) in methanol (20 mL) was added sodium borohydride (144 mg, 3.8 mmol) portionwise. The reaction mixture was stirred for one hour and quenched with water (5 mL). The reaction was concentrated, diluted with methylene chloride and washed with water. The organic phase was concentrated and the crude alcohol purified by flash chromatography on silica (5% to 30% ethyl acetate/hexanes gradient) to provide 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-ol (255 mg, 50%) as a light brown solid: 1H-NMR (DMSO-d6): δ 10.99 (s, 1H), 7.54 (d, 1H), 7.25 (d, 1H), 7.12 (dd, 1H), 5.18 (d, 1H), 4.75-4.70 (m, 1H), 2.64-2.53 (m, 2H), 2.02-1.91 (m, 2H), 1.77-1.66 (m, 2H); MS m/z (M−1) 339, 341.

Workup

  1. customquenched with water (5 mL)
  2. concentrationThe reaction was concentrated
  3. additiondiluted with methylene chloride
  4. washwashed with water
  5. concentrationThe organic phase was concentrated
  6. customthe crude alcohol purified by flash chromatography on silica (5% to 30% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-f95f022e8a9a44298381048a8f5bce86
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

Loading…