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Sodium borohydride → (2-{[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanol

HRID 2075081
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2075081
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[BH4-].[Na+]>CO>[F:41][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[CH:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[OH:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1
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Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 58968633(2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanone

Produkt 1

HCID 58968665(2-{[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanolAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A solution of (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanone (152 mg; 0.256 mmol) and sodium borohydride (22 mg; 0.582 mmol) in methanol (1.5 mL) was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate, washed twice with water and then brine. The organic layer was dried sodium sulfate and concentrated under reduced pressure. The residue was purified over 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 20-50% ethyl acetate in heptane) to give 152 mg (99.7% yield) of the title compound as a colorless gum. MS (ES+): Calc: 595.5, Found: 596.1 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.66 (s, 2H), 7.57 (d, J=8.30 Hz, 1H), 7.55 (d, J=8.30 Hz, 1H), 7.36 (s, 1H), 4.88 (d, J=15.77 Hz, 1H), 4.79 (d, J=15.77 Hz, 1H), 4.76 (d, J=15.77 Hz, 1H), 4.70 (d, J=16.18 Hz, 1H), 4.66 (d, J=7.05 Hz, 1H), 4.21 (s, 3H), 2.20 (bs, 1H), 1.94 (d, J=12.45 Hz, 1H), 1.78 (m, 1H), 1.69-1.51 (m, 4H), 1.2-0.88 (m, 4H).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed twice with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified over 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 20-50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-54967d4a3d5e48ceb936e73c3bf3c703
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07919506B2

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