Hydrazine hydrate (1:1) → Tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[N:10]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>C1COCC1.CO>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]([NH2:10])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
To a stirred solution of [2-(3-chloro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-carbamic acid tert-butyl ester (2.5 g, 6.2 mmol) in THF (10 mL) and methanol (10 mL) was added hydrazine hydrate (3.1 g, 62 mmol). The mixture was heated at 55° C. for 1 hour. Then it was concentrated to dryness, dissolved in H2O (5 mL) and extracted with ethyl acetate (50 mL). The organic mixture was concentrated and purified by column chromatography (methanol:dichloromethane, 1:100) to afford [2-amino-2-(3-chloro-phenyl)-ethyl]-carbamic acid tert-butyl ester. (Yield 1.325 g, 79%). LC-MS: [M+H]+ 271.
Workup
- concentrationThen it was concentrated to dryness
- dissolutiondissolved in H2O (5 mL)
- extractionextracted with ethyl acetate (50 mL)
- concentrationThe organic mixture was concentrated
- custompurified by column chromatography (methanol:dichloromethane, 1:100)
Sources & evidence
- ORD record
- ord-efee358e6d684cb6becdc78fccb7a240
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362023B2
Reaction notes
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