Benzylamine → Ethyl (1R,2R,3S,6S)-6-[(benzylamino)methyl]-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylate

HRID 2245249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245249
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH:22]=O)[C@@H:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C@@H:17]2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:38]([NH:45][CH2:22][C@@H:19]1[C@@H:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C@H:17]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@@H:16]([O:15][C@@H:13]([C:5]2[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=[C:3]([C:2]([F:37])([F:36])[F:1])[CH:4]=2)[CH3:14])[CH2:21][CH2:20]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628113Ethyl(1S,2R,3S,6S)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)-6-formylcyclohexanecarboxylate

Produkt 1

HCID 86628114Ethyl (1R,2R,3S,6S)-6-[(benzylamino)methyl]-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of aldehyde obtained from Step C (0.45 g, 0.84 mmol), benzyl amine (0.093 mL, 0.85 mmol), sodium triacetoxy borohydride (0.55 g, 2.6 mmol) in 30 mL dichloromethane was stirred at room temperature for 12 hr. The reaction mixture was washed with 2 N aq. NaOH, brine, dried over MgSO4, filtered and the solvent was removed under vacuum to give the title compound (0.51 g) which was used without further purification. MS: (MH)+ 626.6.

Aufarbeitung

  1. washThe reaction mixture was washed with 2 N aq. NaOH, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d2ebb5741dc04750a3703540432101cc
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683068B2

Notizen zur Reaktion

Wird geladen…