2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → (+)-2-Chloro-n-[{1-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide

HRID 20810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20810
[Cl:1][C:2]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][C:3]=1[C:4]([NH:6][CH:7]([C:14]1([NH:19][CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[Si:29]([O:36][CH2:37][CH:38]=O)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:24]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:22]=[CH:21][C:3]=1[C:4]([NH:6][CH:7]([C:14]1([N:19]([CH2:38][CH2:37][O:36][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59347824(+/-)-2-Chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide

Produkt 1

HCID 59347865(+)-2-Chloro-n-[{1-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamideAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound (0.390 g, 99%) was prepared from (±)-2-chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide (0.282 g; 0.686 mmol), (tert-butyldimethylsilyloxy acetaldehyde (90%; 0.265 g; 1.52 mmol) and sodium triacetoxyborohydride (0.290 g; 1.52 mmol) in DCM (5 ml) in a similar manner to that described in E30. Mass Spectrum (Electrospray LC/MS). Found 569 (MH+). C29H4035ClF3N2O2Si requires 568. Ret. time: 3.04 min.

Quellen und Nachweise

ORD-Eintrag
ord-1b6c266b36d24e5ea66f57aad432bce0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745642B2

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