Hydrazine → 1,1-Dimethylethyl (3-amino-4-phenylbutyl)carbamate

HRID 1845352Notes

Reaction equation

HRID 1845352 reaction equation
NN.CC([N:7]([CH2:11][CH2:12][CH:13]([N:21]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8](=[O:10])[O-:9])(C)C>C1COCC1.CO>[NH2:21][CH:13]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:12][CH2:11][NH:7][C:8](=[O:10])[O:9][C:15]([CH3:20])([CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 866335391,1-dimethylethyl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutyl]carbamate

Product 1

HCID 597772381,1-Dimethylethyl (3-amino-4-phenylbutyl)carbamateYield 198.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

NH2NH2 (577 uL, 18.4 mmol) was added to a THF/MeOH (1:1, 10 mL) solution of 1,1-dimethylethyl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-phenylbutyl]carbamate (725 mg, 1.84 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 (483 mg, quant.) as a white solid: LC-MS (ES) m/z=264 (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-7d4c88ed77b147979d982111fa6e1d1b
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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