(R)-tert-Butyl 1-azido-3-ethoxypropan-2-ylcarbamate → tert-butyl N-((2R)-1-amino-3-ethoxypropan-2-yl)carbamate

HRID 2092809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092809
[N:1]([CH2:4][C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9]

Komponenten

4

Edukt 1

HCID 86654722(R)-tert-Butyl 1-azido-3-ethoxypropan-2-ylcarbamate

Produkt 1

HCID 86654723tert-butyl N-((2R)-1-amino-3-ethoxypropan-2-yl)carbamateAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A mixture of (R)-tert-butyl 1-azido-3-ethoxypropan-2-ylcarbamate (1.2 g, 4.91 mmol) in MeOH (10 mL) was added palladium on carbon (0.523 g, 4.91 mmol). The mixture was stirred under hydrogen atmosphere overnight at RT. The resulting crude material was reconstituted in MeOH (1.0 mL) and purified via reverse phase preparative HPLC. The fractions were collected and solvent was stripped to dryness via rotary evaporation to give the title compound as clear oil (722 mg, 67%). [M+H] calc'd for C10H22N2O3, 219. found, 219.

Aufarbeitung

  1. custompurified via reverse phase preparative HPLC
  2. customThe fractions were collected
  3. customsolvent was stripped to dryness via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-08c378e9c2e64f638ebe70e3eb79aab6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440689B2

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