Sodium borohydride → Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(hydroxymethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 217529

Reaktionsgleichung

Reaktionsgleichung von HRID 217529
[BH4-].[Na+].[F:3][C:4]([F:43])([F:42])[C:5]1[CH:6]=[C:7]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:8][N:9]([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]1[CH:30]=[C:29]([CH:31]=[O:32])[CH:28]=[CH:27][C:26]=1[O:33][CH3:34])[C:10](=[O:13])[O:11][CH3:12]>CO>[F:3][C:4]([F:42])([F:43])[C:5]1[CH:6]=[C:7]([CH:35]=[C:36]([C:38]([F:40])([F:39])[F:41])[CH:37]=1)[CH2:8][N:9]([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]1[CH:30]=[C:29]([CH2:31][OH:32])[CH:28]=[CH:27][C:26]=1[O:33][CH3:34])[C:10](=[O:13])[O:11][CH3:12]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 11699919Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-formyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Produkt 1

HCID 11585167Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(hydroxymethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (9.9 mg, 0.262 mmol) was added to a solution of methyl [3,5-bis(trifluoromethyl)benzyl]{[5′-formyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (Example 73, 78 mg, 0.131 mmol) in methanol at room temperature. The reaction was stirred for one hour, then solvent was removed in vacuo. The title compound was obtained by column chromatography using 3:7 acetone/hexane. 1H NMR (CDCl3, 500 MHz) δ 7.25 (s, 1H), 7.30-7.62 (m, 6H), 7.08 (m, 1H), 6.94 (m, 1H), 4.64 (s, 2H), 4.15-4.40 (m, 4H), 3.64-3.74 (m, 6H). LC-MS (M-17) 578.0 (4.09 min).

Aufarbeitung

  1. customsolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b70b6b2b66494c6eac409f46857c2c4e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193365B2

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