(2R, 3S)-N-[(tert-Butyloxy)carbonyl]-3-amino-4-phenyl-2-(triisopropylsilyloxy) butan-1-ol → (2R 3S)-N-[(tert-butyloxy)carbonyl]-3-amino-2-(triisopropylsilyloxy)-4-cyclohexyl-1-butanol

HRID 651458

Reaktionsgleichung

Reaktionsgleichung von HRID 651458
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:10]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[C@@H:10]([O:13][Si:14]([CH:15]([CH3:16])[CH3:17])([CH:18]([CH3:19])[CH3:20])[CH:21]([CH3:22])[CH3:23])[CH2:11][OH:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

3

Edukt 1

HCID 15281982(2R, 3S)-N-[(tert-Butyloxy)carbonyl]-3-amino-4-phenyl-2-(triisopropylsilyloxy) butan-1-ol

Produkt 1

HCID 15281983(2R 3S)-N-[(tert-butyloxy)carbonyl]-3-amino-2-(triisopropylsilyloxy)-4-cyclohexyl-1-butanolAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The monosilylated diol of Step 2 was hydrogenated with 5% Rh-C at 60 psi and 60° C. in MeOH (135 mL). The mixture was filtered and the filtrate evaporated. The residue was purified by chromatography, eluting with (15% EtOAc in hexane) to give the title alcohol (8.70 g, 67% yield, mp 61-63° C). The 1H, 13C, and APT NMR spectral data were consistent with the proposed product.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customThe residue was purified by chromatography
  4. washeluting with (15% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4bf9f75cd87d4fc49907c4b095d29576
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281235B1

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