Sodium triacetoxyborohydride → (S)-(1-{[4,4-Bis-(4-fluoro-phenyl)-butylamino]-methyl}-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

HRID 990399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990399
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:3]=1.[C:20]([O:24][C:25](=[O:35])[N:26]([C@H:28]([CH:33]=O)[CH2:29][CH:30]([CH3:32])[CH3:31])[CH3:27])([CH3:23])([CH3:22])[CH3:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOC(C)=O>[C:20]([O:24][C:25](=[O:35])[N:26]([C@H:28]([CH2:33][NH:12][CH2:11][CH2:10][CH2:9][CH:8]([C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:29][CH:30]([CH3:31])[CH3:32])[CH3:27])([CH3:23])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 13530069HCID 13530069, VerbindungHCID 54220075(S)-(1-Formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

Produkt 1

HCID 54125409(S)-(1-{[4,4-Bis-(4-fluoro-phenyl)-butylamino]-methyl}-3-methyl-butyl)-methyl-carbamic acid tert-butyl esterAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4,4-bis-(4-fluorophenyl)-butylamine (200 mg, 0.77 mmol) was dissolved in CH,2Cl2 (5 mL), treated with (S)-(1-formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester (229 mg, 1.0 mmol), stirred for 30 minutes, then cooled to 0° C., treated with NaBH(OAc)3 (245 mg, 1.16 mmol), and stirred overnight at room temperature. The reaction was diluted with EtOAc (100 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated. The crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2 to give 257 mg (70%) of the desired product as an oil. MS: 475.4 (M+1 for C28H40N2O2F2); an oil; TLC (SiO2), Rf 0.26 (4% MeOH/CH2Cl2); HPLC (1:1 CH3CN/H2O with 0.1% TFA, C-18 column) 100%, RT=15.013 min.

Aufarbeitung

  1. stirringstirred overnight at room temperature
  2. washwashed with saturated bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-5d77ad6fed0f43758ee948cbb70c46b3
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458781B1

Notizen zur Reaktion

Wird geladen…