Triethylamine → HCID 15592690, compound

Participants

Reaction Steps

A stirred solution of 1.28 g (3.08 mmol) of the [S-(R*,S*)] carbamate from Step A, 0.52 ml (380 mg, 3.7 mmol) of triethylamine, and 0.34 ml (460 mg, 3.4 mmol) of trichlorosilane in 12 ml of toluene under a nitrogen atmosphere was heated at 60° C. for 2 hours. The reaction mixture was then diluted with 50 ml of saturated aqueous NH4Cl and extracted with ether (3×25 ml). After being dried (MgSO4), the combined organic extracts were concentrated under reduced pressure and chromatography of the residue on 20 g of silica gel with 1:15 ethyl acetate/hexane afforded 667 mg (81%) of the title compound as a white solid melting at 51.5°-53.5° C.: [α]D22 =+2.0° (CHCl3, c 1.00) and [α]36522 =+4.8° (CHCl3, c 1.00). The spectral and chromatographic properties of this material were identical to those of racemic material prepared in Example 1 (Step C).

Provenance & Evidence