[(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester → (1S)-1-(t-butyldiphenylsilyloxymethyl)propylamine

HRID 891632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891632
C(OC(=O)[NH:10][C@H:11]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:12][CH3:13])C1C=CC=CC=1>CO.[Pd]>[Si:16]([O:15][CH2:14][C@@H:11]([NH2:10])[CH2:12][CH3:13])([C:29]([CH3:31])([CH3:32])[CH3:30])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 1

HCID 60109785[(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester

Produkt 1

HCID 23598348(1S)-1-(t-butyldiphenylsilyloxymethyl)propylamineAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester (3.70 g, 8.00 mmol) (obtained as described in Reference Example 34(1)) in methanol (185 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (3.70 g) at room temperature for 4 hours. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride:methanol (9:1) as the eluant to afford (1S)-1-(t-butyldiphenylsilyloxymethyl)propylamine (2.32 g, yield 88%) as a colorless oil.

Aufarbeitung

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered in order
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-fca0f4af0c1846d7bf069eb9c05244f6
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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