tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate → 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine

HRID 1670618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670618
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([NH:14]CC2C=CC=CC=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)CCC.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([NH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 11277777tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 104654571-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidineAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 2631-ButanolLösungsmittel

Versuchsvorschrift

To a solution of (3S,4S)-3-benzylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.054 mol, 16.0 g) in n-butanol (225 mL) add 10% Pd/C (5.0 g) and hydrogenate the mixture at 50 psi for 10 h. Filter the reaction mixture thorough a plug of diatomaceous earth and wash with ethanol. Evaporate the filtrate to obtain the title compound as a white solid (11.10 g, 99%). APCI MS m/z 203 [M+H]+; [α]23D +7.8° (c, 0.50, MeOH).

Aufarbeitung

  1. filtrationFilter the reaction mixture thorough a plug of diatomaceous earth
  2. washwash with ethanol
  3. customEvaporate the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-dba5d7cbccb1442f95d9a897d4448397
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994164B2

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