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

HRID 1194901

Reaction equation

HRID 1194901 reaction equation
[CH3:1][C@@H:2]1[CH2:7][C@H:6]([OH:8])[C@@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O/[N:32]=[C:33](/[C:39](=[O:41])[CH3:40])\[C:34]([O:36][CH2:37][CH3:38])=[O:35].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:1][C@@H:2]1[CH2:7][C@@H:6]([O:8]/[N:32]=[C:33](/[C:39](=[O:41])[CH3:40])\[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C@@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 165675(+)-MentholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178472876HCID 178472876, compound

Product 1

HCID 177701097ethyl (2Z)-2-[(1R,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxyimino-3-oxobutanoateYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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)].

Sources & evidence

ORD record
ord-ff99fa30d5ed4ace9bfa212ac8548c65
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Linked notes

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