Hydrazine hydrate (1:1) → tert-butyl N-(2-amino-2-phenylethyl)carbamate

HRID 1809663Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH:9]([N:16]1C(=O)C2C(=CC=CC=2)C1=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>C1COCC1.CO>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH:9]([NH2:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (23 g, 63 mmol) in THF (180 mL) and MeOH (180 mL) was added 85% hydrazine hydrate (37 mL, 630 mmol) slowly. The resulting mixture was heated at 65° C. for 15 hours. The reaction mixture was cooled to room temperature, then concentrated to dryness. The residue was purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3H2O) to give (2-amino-2-phenyl-ethyl)-carbamic acid tert-butyl ester as a white solid. (Yield 7.4 g, 50%).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated to dryness
customThe residue was purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3H2O)

Sources & evidence

ORD record: ord-b5b075ff7cb14d56a9510ddd3586399c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362023B2

Reaction notes

Loading…