HCID 68743595, compound → HCID 59212645, compound

HRID 1191916Notes

Reaction equation

HRID 1191916 reaction equation
[C:1]([C:3]1([N:16]2[CH2:21][CH2:20][N:19]([CH:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=4)[CH2:24][CH2:23]3)[C@@H:18]([CH3:35])[CH2:17]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#N.C[Mg]Br>C1COCC1.CCOCC>[CH3:1][C:3]1([N:16]2[CH2:21][CH2:20][N:19]([CH:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=4)[CH2:24][CH2:23]3)[C@@H:18]([CH3:35])[CH2:17]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 68743595HCID 68743595, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59212645HCID 59212645, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-cyano-4-{(3S)-3-methyl-4-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazin-1-yl}piperidine-1-carboxylate (0.72 g, 1.3 mmol) in THF (20 mL) was added a 3 M solution of methylmagnesium bromide in ether (4.0 mL). After being stirred at room temperature overnight, the reaction was quenched by addition of water. The resulting solution was extracted with EtOAc twice. The combined EtOAc layers were dried and concentrated. Column chromatography on silica (20-30% EtOAc in hexane) provided the title compound (0.32 g, 50%) as a viscous oil. MS calculated for C26H38F3N3O2: (M+H)+ 482. found 482.3.

Workup

  1. customthe reaction was quenched by addition of water
  2. extractionThe resulting solution was extracted with EtOAc twice
  3. dry with materialThe combined EtOAc layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6290f23eecf04939a29fca9ef05860d5
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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