Nitrogen → (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate

HRID 1254217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1254217
[N:1]([CH2:4][C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[N+]=[N-].N#N>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

5

Edukt 2

HCID 947NitrogenHCID 59382971(S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate

Produkt 1

HCID 10988904(S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamateAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate (7.2 g, 25.5 mmol) in methanol (250 mL) was added to wetted Pd/C (1.0 g) in a N2-filled Parr bottle. After 3 vac/purge cycles with H2, the vessel was charged to 50 psi and shaken on a Parr apparatus overnight. Theoretical equivalents (36 psi) of H2 were consumed. The reaction mixture was filtered through a pad of Celite and the solvent was removed to give (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate (5.9 g, 90%) as a white solid. 1H NMR (D6-DMSO) δ 0.70-1.30 (m 10H), 1.38 (s, 9H), 1.58 (d, 2H), 1.80 (d, 1H), 2.66 (m, 1H), 2.78 (d, 1H), 3.74 (m, 1H), 6.77 (d, 1H), 8.0 (bs, 2H). MS ESI +ve m/z 157 (M(−BOC)+1).

Aufarbeitung

  1. additionfilled Parr bottle
  2. customAfter 3 vac/purge cycles with H2
  3. additionthe vessel was charged to 50 psi
  4. customTheoretical equivalents (36 psi) of H2 were consumed
  5. filtrationThe reaction mixture was filtered through a pad of Celite
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-128650d90ecc4ef9b5616a591a67c812
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455521B2

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