Diethyl Ether → ((S)-1-Aminomethyl-5-benzyloxy-3,3-dimethyl-pentyl)-carbamic acid tert-butyl ester
Reaction equation
NN.[C:3]([O:7][C:8](=[O:37])[NH:9][C@H:10]([CH2:25][N:26]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:11][C:12]([CH3:24])([CH3:23])[CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:6])([CH3:5])[CH3:4].C(OCC)C>C1COCC1.C(O)C>[C:3]([O:7][C:8](=[O:37])[NH:9][C@H:10]([CH2:25][NH2:26])[CH2:11][C:12]([CH3:24])([CH3:23])[CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:4])([CH3:6])[CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
Hydrazine (66.6 ml of a 1M solution in THF, 66.6 mmol) is added to a suspension of [(S)-5-benzyloxy-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3,3-dimethyl-pentyl]-carbamic acid tert-butyl ester (4 g, 8.32 mmol) in ethanol (100 ml), and the resulting solution is heated at 40° C. overnight. A fluffy white precipitate forms. The reaction is allowed to cool to room temperature and diethyl ether (100 ml) is added and the resulting white suspension cooled at 0° C. for 30 minutes. The white precipitate is removed by filtration and the solvent removed in vacuo. The residue is then stirred with diethyl ether (100 ml) for 1 hour, filtered and the solvent is removed in vacuo to afford ((S)-1-Aminomethyl-5-benzyloxy-3,3-dimethyl-pentyl)-carbamic acid tert-butyl ester as a pale yellow oil; [M+H]+ 351.
Workup
- temperatureto cool to room temperature
- temperaturethe resulting white suspension cooled at 0° C. for 30 minutes
- customThe white precipitate is removed by filtration
- customthe solvent removed in vacuo
- filtrationfiltered
- customthe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-f7dceba3f36d4d18adb67e494febe26b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697687B2
Reaction notes
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