Oxygen → HCID 46843534, compound

Participants

Reaction Steps

In a glove box (O2 content≦2 ppm) a 35 ml autoclave equipped with a glass insert and a magnetic stirring bar was charged with 250 mg (0.835 mmol) of 6-(3-Fluoro-phenylsulfanyl)-3,4-dihydro-naphthalene-1-carboxylic acid amide, 4.03 mg (0.00418 mmol) of [Ru(trifluoroacetate)2((S)-pTol-MeOBIPHEP)] (S/C 200) and 3 ml of methanol. The asymmetric hydrogenation was run for 24 h at 40° C. under 40 bar of hydrogen. After cooling to room temperature the pressure was released from the autoclave, the methanol solution was evaporated in vacuo. The residue was dissolved in 4 ml of dichloromethane and filtered through a silicagel pad, which was washed with a total of 6 ml of dichloromethane. Evaporation of the filtrate and drying (50° C./10 mbar/2 hours) afforded 232 mg of (R)-6-(3-Fluoro-phenylsulfanyl)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid amide as a light yellow solid with an enantiomeric ratio of 99:1. The conversion was >=99.9%.

Provenance & Evidence