Triphenylphosphine → ethyl (2Z)-2-[(1R,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxyimino-3-oxobutanoate

(1S, 2R, 5S)-(+)-Menthol (7.03 g, 45 mmol), triphenylphosphine (8.65 g, 33 mmol), ethyl (Z)-2-hydroxyimino-3-oxobutyrate (4.77 g, 33 mmol) and diethyl azodicarboxylate (5.7 g, 33 mmol) were reacted by analogy with Example 4a Method 3 to give the title compound (1.37 g, 14%), νmax (CH2Cl2) 2960, 2930, 2870, 1745, 1690, 1370, 1320, 1235, 1075, and 1010cm-1 ; δH (400 MHz, CDCl3) 0.87 (3H, d, J 6.6 Hz), 0.90 (3H, d, J 6.8 Hz), 0.92 (3H, d, J 6.7 Hz), ca 0.9 (1H, m), 1.02-1.12 (2H, m), 1.1-1.3 (1H, m), 1.32 (3H, t, J 7.1 Hz), 1.50-1.65 (2H, m), 1.67-1.78 (2H, m), 2.06-2.18 (1H, m), 2.40 (1H, s), 4.34 (2H, dq, J 7.1 and 1.0 Hz), and 4.70 (1H, broad s); δ13C (100 MHz, CDCl3), 14.24 (CH3), 20.70 (CH3), 20.97 (CH3), 22.26 (CH3) 25.04 (CH2), 25.11 (CH3) 26.06 (CH), 29.10 (CH), 34.77 (CH2), 39.44 (CH2) 46.98 (CH), 61.70 (CH2), 83.43 (CH), 150.28, 161.53, 192.94 [Ammonia CI mass spectrum Found: MH+ (298); MNH+ (315)].

ORDレコード

ord-ff99fa30d5ed4ace9bfa212ac8548c65

出典データセット

uspto-grants-1989_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04816452