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

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole	HCID 2734713	—
Reactant	4-Methyl-1-indanone	HCID 4418431	—
Reactant	(Dimethyl sulfide)trihydroboron	HCID 12423031	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(1R)-2,3-Dihydro-4-methyl-1H-inden-1-ol	HCID 11629630	—

Reaction Conditions

Temperature	-30 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07884244B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-aa22e2fdcb89479da58dee5e55d34ed0
Source note	uspto-grants-2011_02