Trichloroacetimidic acid (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl ester → Diethyl (1S,2S,3R,4S)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(2-methylphenyl)cyclohexane-1,2-dicarboxylate

HRID 1393328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1393328
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]1[C@@H:13]([OH:14])[CH2:12][CH2:11][C@H:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@H:9]1[C:20]([O:22][CH2:23][CH3:24])=[O:21].[F:25][C:26]([F:47])([F:46])[C:27]1[CH:28]=[C:29]([C@@H:37](OC(=N)C(Cl)(Cl)Cl)[CH3:38])[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1>>[F:25][C:26]([F:46])([F:47])[C:27]1[CH:28]=[C:29]([C@H:37]([O:14][C@H:13]2[CH2:12][CH2:11][C@H:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@@H:9]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C@@H:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH3:38])[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=1

Komponenten

3

Edukt 2

HCID 11611082Trichloroacetimidic acid (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl esterHCID 66774775Diethyl(1S,2S,3R,4S)-3-(2-methylphenyl)-4-hydroxycyclohexane-1,2-dicarboxylate

Produkt 1

HCID 86599803Diethyl (1S,2S,3R,4S)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(2-methylphenyl)cyclohexane-1,2-dicarboxylate

Versuchsvorschrift

The title compound was prepared from the first eluting isomer diethyl(1S,2S,3R,4S)-3-(2-methylphenyl)-4-hydroxycyclohexane-1,2-dicarboxylate (step G) and (1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl-2,2,2-trichloroethanimidoate (Example 6, step E) according to the procedure of Example 6, step F. 1H-NMR (CDCl3): δ: 7.65 (1 H, s), 7.15 (2 H, s), 7.08-6.92 (4 H, m), 4.25 (1 H, q, J=6.0 Hz), 4.20-4.10 (2 H, m), 3.85-3.66 (2 H, m), 3.42 (1 H, m), 3.21 (1 H, t), 2.90-2.79 (2 H, m), 2.35 (1 H, m), 2.25 (1 H, m), 2.22 (3 H, s), 1.69-1.56 (2 H, m), 1.30 (3 H, d, J=6.0 Hz), 1.23 (3 H, t, J=7.2 Hz), 0.77 (3 H, t, J=7.2 Hz). Unreacted starting alcohol could be recovered by flushing the column with EtOAc and reused in the above reaction.

Aufarbeitung

  1. customcould be recovered
  2. customby flushing the column with EtOAc
  3. customreused in the above reaction

Quellen und Nachweise

ORD-Eintrag
ord-ccb4e2cec1514eafbb03e8f188c0bd22
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345083B2

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