Hydrazine → Tert-butyl 3-amino-3-phenylpropylcarbamate

HRID 1960972Notes

Reaction equation

HRID 1960972 reaction equation
NN.CC([N:7]([CH2:11][CH2:12][CH:13]([N:20]1C(=O)C2C(=CC=CC=2)C1=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8](=[O:10])[O-:9])(C)C>C1COCC1.CO>[NH2:20][CH:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:12][CH2:11][NH:7][C:8](=[O:10])[O:9][C:14]([CH3:19])([CH3:15])[CH3:13]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86633537HCID 86633537, compound

Product 1

HCID 57826906Tert-butyl 3-amino-3-phenylpropylcarbamateYield 151.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

NH2NH2 (1.8 mL, 57.7 mmol) was added to a THF/MeOH (1:1, 30 mL) solution of 1,1-dimethylethyl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl]carbamate (2.2 g, 5.79 mmol) and stirred at 50° C. in a sealed system. After 12 hours, the solids were filtered, washing with methanol. The filtrate was concentrated and purified by column chromatography using 5% MeOH in CHCl3 containing 1% NH4OH to give the title compound (1.1 g, 76%) as a white solid: LC-MS (ES) m/z=251 (M+H)+.

Workup

  1. filtrationthe solids were filtered
  2. washwashing with methanol
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-503cf62766864a15b87bcd3ce56fe639
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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