HCID 58818860, compound → HCID 58818861, compound

Participants

Reaction Steps

R,R-DIPAMP cyclooctadiene Rh(I) tetrfluoroborate (190 mg, 0.25 mmol, 0.04 eq) was added to a solution of (Z)-2-benzyloxycarbonylamino-5,5-dimethyl-hepta-2,6-dienoic acid methyl ester (2.00 g, 6.30 mmol, 1.00 eq) in dry methanol (20 mL) in a Paar hydrogenation flask. The reaction vessel was evacuated and flushed with a hydrogen atmosphere three times, then vigorously shaken under 50 psi of hydrogen overnight. The reaction mixture was concentrated in vacuo then filtered through a plug of silica gel using a gradient of ethyl acetate in hexanes as the eluant to provide (S)-2-benzyloxycarbonylamino-5,5-dimethyl-heptanoic acid methyl ester as a yellow oil (1.63 g, 81% yield); 1H NMR (CDCl3, 400 MHz) δ 0.74-0.90 (m, 9H), 1.10-1.30 (m, 4H), 1.58-1.70 (m, 1H), 1.75-1.90 (m, 1H), 3.75 (s, 3H), 4.30-4.40 (m, 1H), 5.14 (s, 2H), 5.24-5.33 (m, 1H), 7.30-7.37 (m, 5H); [α]20D=+15.57 c=2.00, CHCl3.

Provenance & Evidence