Acetic Acid → (+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

HRID 1165655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165655
[CH3:1][C@:2]([N+:8]([O-])=O)([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4].[C:11]([OH:14])(=[O:13])[CH3:12]>CCO.[Pd]>[C:11]([OH:14])(=[O:13])[CH3:12].[NH2:8][C@@:2]([CH3:1])([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 13375425(+-)(2R*,3R*)-2-Methyl-2-nitro-1,3-butanediol

Produkt 1

HCID 86741969(+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of (±)-(2R*,3R*)-2-methyl-2-nitro-1,3-butanediol (32B, 13.93 g, 0.093 mol) in 95% EtOH (120 mL) was added glacial acetic acid (17 mL) and 10% Pd/C (MCB, 1.0 g). The mixture was reduced in a Parr apparatus at 50 psi of H2 for 48 h. The catalyst was then removed by filtration on a Celite® pad and the solvent removed to give the crude amine salt. Three portions of PhCH3 (50 mL) were added to the flask and removed by rotary evaporation to remove final traces of H2O and acetic acid. The residue, a viscous oil gradually solidified under high vacuum. The solie was triturated with Et2O, filtered and the resulting solid further washed with Et2O to give after drying, 16.23 g (97%) of (±)-(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate, mp 117°-121°, (C,H,N).

Aufarbeitung

  1. customThe catalyst was then removed by filtration on a Celite® pad
  2. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-4295bad2369d4da2a1ecf2e24495406a
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910218

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