Diisopropylethylamine → Methyl 3-(S)-((3,5-bis(trifluoromethyl)phenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate

HRID 1289962Notes

Reaction equation

HRID 1289962 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([C:7]([O:9][CH3:10])=[O:8])[C@H:3]1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C.[F:27][C:28]([F:42])([F:41])[C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:32]Br>C(#N)C>[F:27][C:28]([F:41])([F:42])[C:29]1[CH:30]=[C:31]([CH2:32][NH:1][C@H:2]2[CH2:6][CH2:5][C@H:4]([C:7]([O:9][CH3:10])=[O:8])[C@H:3]2[C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 22885811Methyl 3-(S)-(amino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate

Product 1

HCID 86752554Methyl 3-(S)-((3,5-bis(trifluoromethyl)phenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylateYield 71.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 20 mg of amine from Example 63, 0.050 mL of DIPEA and 30 mg of 3,5-bis(trifluoromethyl)benzyl bromide in 1 mL of acetonitrile was stirred for 20 h in a sealed vial and evaporated. The residue was purified on a 1 mm preparative silica gel plate eluted with 20% ethyl acetate in hexanes to obtain 28 mg of title compound as an oil. Mass spec (NH3 /CI): 464 (M+1).

Workup

  1. customevaporated
  2. customThe residue was purified on a 1 mm preparative silica gel plate
  3. washeluted with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c21f6231f207408e8c93a51e3af7f788
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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