Methanol → (1R)-2,3-Dihydro-4-methyl-1H-inden-1-ol

HRID 1363677Notes

Reaction equation

HRID 1363677 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.B.CSC.CO>C1COCC1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C@H:6]2[OH:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 44184314-Methyl-1-indanoneHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 11629630(1R)-2,3-Dihydro-4-methyl-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 4-methyl-indan-1-one (5.00 g, 34.20 mmole) and (S)-2-methyl-CBS-oxazaborolidine (5.00 mL, 1.0 M in THF, 5.00 mmol) in THF at −20° C. was added borane-methylsulfide (12.00 mL, 1.0 M in THF, 12.00 mmol) over 20 minutes. The resulting mixture was then stirred for 50 minutes and cooled to −30° C. Methanol (40.00 mL) was added and the resulting mixture was gradually warmed to room temperature and concentrated to give the crude alcohol.

Workup

  1. temperaturethe resulting mixture was gradually warmed to room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-aa22e2fdcb89479da58dee5e55d34ed0
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

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