Hydrazine hydrate (1:1) → (S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanamine
Reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:19]1C(=O)C2C(=CC=CC=2)C1=O)[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1.CO.O.NN>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=1)[NH2:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 66 (14.35 g, 33.07 mmol) and THF/MeOH (1:1, 400 mL) was added hydrazine monohydrate (4.138 g, 82.67 mmol) and the reaction was heated to 60° C. for 3 h. The reaction was diluted with THF and filtered. The solid was discarded and the filtrate was concentrated and the residue dissolved in ether (200 mL). The organic layer was washed twice with water (100 mL). The organic layer was then dried, filtered and concentrated. The crude product was purified by SiO2 (Biotage 65) eluting with an EtOAc/hexane gradient (30 to 40% EtOAc) to afford 8.85 g (88.1%) of (S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanamine (68).
Workup
- filtrationfiltered
- concentrationthe filtrate was concentrated
- dissolutionthe residue dissolved in ether (200 mL)
- washThe organic layer was washed twice with water (100 mL)
- customThe organic layer was then dried
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by SiO2 (Biotage 65)
- washeluting with an EtOAc/hexane gradient (30 to 40% EtOAc)
Sources & evidence
- ORD record
- ord-95207e8033b44c8b936dceda5caea946
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133187B2
Reaction notes
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