Sodium triacetoxyborohydride → HCID 68828337, Verbindung

HRID 2099351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099351
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C@H:7]([C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])[CH2:15]3)=[O:10])[NH2:8])=[CH:4][CH:3]=1.[C:35]([N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C:43]1=O)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([NH:8][CH:45]2[CH2:46][CH2:47][N:42]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:43][CH2:44]2)[C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[C:20]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[O:21])[CH2:15]3)=[O:10])=[CH:33][CH:34]=1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 68829063HCID 68829063, Verbindung

Produkt 1

HCID 68828337HCID 68828337, VerbindungAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.41 g of N-[8-(4-chloro-D-phenylalanyl)-8-azabicyclo[3.2.1]oct-3-yl]-N-cyclohexyl-N′,N′-diethylurea is dissolved in 4 ml of dichloromethane under N2 in the presence of 0.17 g of N-BOC-piperidone and of 0.23 g of sodium triacetoxyborohydride, and the mixture is stirred at ambient temperature for 16 h. After evaporation and hydrolysis, extraction is carried out with ethyl acetate until the aqueous phase is completely depleted. The organic phase is washed with H2O and then with a saturated aqueous sodium chloride solution. Drying over MgSO4 and concentration to dryness are carried out. The crude is chromatographed on silica gel, elution being carried out with a 98/2 mixture of dichloromethane and methanol. 0.37 g of tert-butyl 4-{[(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]amino}-8-azabicyclo-[3.2.1]oct-8-yl)-2-oxoethyl]amino}piperidine-1-carboxylate is then obtained.

Aufarbeitung

  1. customAfter evaporation and hydrolysis, extraction
  2. washThe organic phase is washed with H2O
  3. dry with materialDrying over MgSO4 and concentration to dryness
  4. customThe crude is chromatographed on silica gel, elution
  5. additionbeing carried out with a 98/2 mixture of dichloromethane and methanol

Quellen und Nachweise

ORD-Eintrag
ord-0b5e6f590b2b48d39c628b6a42fe775f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569582B2

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