(S)-1-(4-Fluorophenyl)-ethylamine → HCID 86629648, compound

HRID 911411Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[C:12](OS(C(F)(F)F)(=O)=O)=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].[F:30][C:31]1[CH:36]=[CH:35][C:34]([C@@H:37]([NH2:39])[CH3:38])=[CH:33][CH:32]=1>>[F:30][C:31]1[CH:36]=[CH:35][C:34]([C@@H:37]([NH:39][C:12]2[C:9]3[CH2:10][CH2:11][N:5]([C:3](=[O:4])[C:2]([F:29])([F:28])[F:1])[CH2:6][CH2:7][C:8]=3[CH:15]=[CH:14][C:13]=2[C:16]([F:19])([F:17])[F:18])[CH3:38])=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 2779063(S)-1-(4-Fluorophenyl)-ethylamine

HCID 574477493-(2,2,2-Trifluoroacetyl)-6-trifluoromethanesulfonyloxy-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86629648HCID 86629648, compoundYield 66.2%

Procedure

Use a method similar to the General Procedure 5-3 to couple 3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (430 mg, 0.94 mmol) with (S)-1-(4-fluorophenyl)ethylamine (195 mg, 1.40 mmol). Purify by chromatography on silica gel eluting with EtOAc/hexane (1:8) to give (S)-6-[1-(4-fluorophenyl)-ethylamino]-3-(2,2,2-trifluoroacetyl)-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (279 mg, 65%). MS (ES+) m/z: 449 (M+H)+.

Workup

customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:8)

Sources & evidence

ORD record: ord-2e4fb9d6c2424fcca6fbbd0fd993ca76
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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