Methanol → HCID 59822021, compound

Participants

Reaction Conditions

Reaction Steps

140 mg (0.96 mmol, 0.08 eq.) of (1R,2S)-1-aminoindan-2-ol are initially charged in 440 ml of THF, and 7.80 g (47.8 mmol, 4.0 eq.) of borane N,N-diethylaniline complex are added at room temperature. After the evolution of gas has ceased, the mixture is cooled to 0° C. and 5.47 g (12 mmol, 1 eq.) of the compound from Example 2A, dissolved in 40 ml of THF, are added. With stirring, the mixture is allowed to warm to room temperature over a period of 28 h. After the reaction has ended, 20 ml of methanol are added to the reaction mixture and the mixture is concentrated. The residue is partitioned between 150 ml of water and 150 ml of ethyl acetate. The aqueous phase is extracted twice with in each case 100 ml of ethyl acetate. The combined organic phases are washed with 50 ml of saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product is then purified by chromatography (silica gel, mobile phase: isohexane/ethyl acetate 4:1).

Provenance & Evidence