Hydrochloric Acid → HCID 87158396, compound

HRID 2206904Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][C:9]1[C:10]([Br:39])=[N:11][C:12]([N:15]2[CH2:19][CH2:18][C:17]([C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[CH:16]2[OH:38])=[CH:13][CH:14]=1)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][C:17]([C:24]3[CH:25]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=3)([C:20]([F:22])([F:23])[F:21])[CH:16]2[OH:38])=[N:11][C:10]=1[Br:39]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of t-butyl[(6-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}-2-bromopyridin-3-yl)methyl]carbamate (0.63 g), ethyl acetate (20 ml) and conc. hydrochloric acid (2 ml) was stirred at 60° C. for 1 hour. After cooling, the mixture was neutralized with sodium carbonate, extracted with ethyl acetate and dried. The solvent was distilled off to obtain 1-[5-(aminomethyl)-6-bromopyridin-2-yl]-3-[3,5-bis-(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-2-ol (0.43 g).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
customdried
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-292c286f388640fa939d0155f1f61c12
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Reaction notes

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