(2S,3S)-2-(N-Benzyloxycarbonylamino)-3-octadecanol → (2S,3S)-2-Amino-3-octadecanol

HRID 722823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722823
C(OC([NH:11][C@H:12]([C@@H:14]([OH:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:13])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@H:12]([C@@H:14]([OH:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:13]

Komponenten

4

Edukt 1

HCID 58743388(2S,3S)-2-(N-Benzyloxycarbonylamino)-3-octadecanol

Produkt 1

HCID 57017700(2S,3S)-2-Amino-3-octadecanolAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of N-benzyloxycarbonylamine 90 (330 mg, 0.79 mmol) in MeOH (40 mL) at room temperature, Pd—C (10% wt, 100 mg, 0.09 mmol) was added. The mixture was purged with a stream of dry Ar, and then H2. The reaction was stirred overnight under a H2 atmosphere (1 atm). The catalyst was filtered off through a 0.45 μm teflon filter in polypropylene housing, washing the filter with MeOH (50 mL) and the solvent was evaporated in vacuo. The crude was purified by column chromatography on silica (90:10 CH2Cl2/MeOH to 100% MeOH) to obtain aminoalcohol 91 as a white solid (200 mg, 89% yield).

Aufarbeitung

  1. customThe mixture was purged with a stream of dry Ar
  2. filtrationThe catalyst was filtered off through a 0.45 μm teflon
  3. filtrationfilter in polypropylene housing
  4. washwashing the
  5. filtrationfilter with MeOH (50 mL)
  6. customthe solvent was evaporated in vacuo
  7. customThe crude was purified by column chromatography on silica (90:10 CH2Cl2/MeOH to 100% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-83630ad523ed493bb455ccf9435fdefb
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138547B2

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