5,6,7,8-Tetrahydro-3,7,7-trimethylquinoline-5-one → HCID 19690962, compound

HRID 1684Notes

Reaction equation

HRID 1684 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][C:9](=[O:12])[C:10]=2[CH:11]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][CH:9]([OH:12])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 41751925,6,7,8-Tetrahydro-3,7,7-trimethylquinoline-5-oneHCID 4311764Sodium borohydride

Product 1

HCID 19690962HCID 19690962, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-one (240 mg, 1.3 mmol) in MeOH (6.5 mL) was cooled to 0° C. under Argon and treated with NaBH4 (48 mg, 1.3 mmol). The reaction was stirred over 14 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil that was chromatographed on a silica gel column packed in 95:5 EtOAc:hexanes and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure to give 5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-ol.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude oil that was chromatographed on a silica gel column
  3. washhexanes and eluted with same
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-997799bff2054cbcbc860fbe74d39dc5
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Reaction notes

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