Ethyl Acetate → [1-Allyl-4-amino-4-(3-bromophenyl)pyrrolidin-3-yl]methanol
Reaction equation
[CH2:1]([N:4]1[CH2:11][CH:10]2[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=3)([NH:7][O:8][CH2:9]2)[CH2:5]1)[CH:2]=[CH2:3].C(OCC)(=O)C>C(O)(=O)C.[Zn]>[CH2:1]([N:4]1[CH2:5][C:6]([NH2:7])([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)[CH:10]([CH2:9][OH:8])[CH2:11]1)[CH:2]=[CH2:3]Participants
5
Procedure
A 22° C. solution of 5-allyl-6a-(3-bromophenyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (40 g, 129.4 mmol) in acetic acid (400 mL) is treated with zinc dust (42.3 g, 646.8 mmol) in one portion. The reaction is stirred vigorously at room temperature for 1 hour. Ethyl acetate (400 mL) is added and the mixture is filtered through diatomaceous earth. The filtrate is evaporated and the residue dried under vacuum. The residue is partitioned in water (300 mL) and MTBE (300 mL). The pH is adjusted to 8 with sodium hydroxide 50% w/w and the organic layer is separated, dried over sodium sulfate, and filtered. The filtrate is evaporated and the residue dried under vacuum to give the title compound (41 g, 97%). ES/MS (m/e): 311 (M+1).
Workup
- filtrationthe mixture is filtered through diatomaceous earth
- customThe filtrate is evaporated
- customthe residue dried under vacuum
- customThe residue is partitioned in water (300 mL)
- customthe organic layer is separated
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customThe filtrate is evaporated
- customthe residue dried under vacuum
Sources & evidence
- ORD record
- ord-5f082fdf4aa8408b8482e07ac463f1f6
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987254B2
Reaction notes
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