(1S,2S)-(1-([benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester → (2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-ol

HRID 1766845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766845
C(OC(=O)[NH:7][C@@H:8]([CH2:14][N:15](C(OCC1C=CC=CC=1)=O)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24])[C@@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])(C)(C)C>CO.[Pd]>[NH2:7][C@H:8]([C@@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])[CH2:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24]

Komponenten

4

Edukt 1

HCID 69287833(1S,2S)-(1-([benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 69287338(2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-olAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (1S,2S)-(1-{[benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester (600 mg, 1.2 mmol, see procedure 12a) in MeOH was charged with 5% Pd/C, Degussa style (120 mg), stirred under H2 (1 atm) for 12 h at RT, filtered, and concentrated in vacuo. The residue was dissolved in methylene chloride (6 mL) and the resultant solution was charged with trifluoroacetic acid (6 mL). The mixture was stirred for 3 h at RT and concentrated in vacuo. The residue was dissolved in benzene and the resultant solution was concentrated in vacuo; this procedure was repeated to provide (2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-ol (321 mg). MS found: (M+H)+=251.4.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride (6 mL)
  4. additionthe resultant solution was charged with trifluoroacetic acid (6 mL)
  5. stirringThe mixture was stirred for 3 h at RT
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in benzene
  8. concentrationthe resultant solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8a5ac248821e42a887670ca5b163bcdd
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230133B2

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