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

HRID 516044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516044
[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-239cc8f0f67e4fe88e7bfe59a829d8b4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108970B2

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