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

HRID 1194901

Reaktionsgleichung

Reaktionsgleichung von HRID 1194901
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(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)].

Quellen und Nachweise

ORD-Eintrag
ord-ff99fa30d5ed4ace9bfa212ac8548c65
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04816452

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