Tetrahydrofuran toluene → HCID 11120080, compound

HRID 1642470Notes

Reaction equation

HRID 1642470 reaction equation
[C:1]([C:3]1([N:16]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][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-].C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[OH:22][CH:19]1[CH2:20][CH2:21][N:16]([C:3]2([CH3:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 59732263HCID 59732263, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 11120080HCID 11120080, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-cyano-4-(4-hydroxy-1-piperidyl)piperidine-1-carboxylate (5.8 g, 18.74 mmol) in THF (40 mL) was added a 1.4 M solution of MeMgBr in toluene/THF (26.8 mL, 37.48 mmol) at 0° C., and the mixture was stirred at room temperature for 12 h. The reaction was then quenched with saturated aqueous ammonium chloride and the mixture was extracted with dichloromethane (2×30 mL). The combined extracts were concentrated in vacuo to afford (5.42 g, 97%) the title compound, which was used for the next step without further purification.

Workup

  1. customThe reaction was then quenched with saturated aqueous ammonium chloride
  2. extractionthe mixture was extracted with dichloromethane (2×30 mL)
  3. concentrationThe combined extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-f0e194f2ea804cb6b8db0e0040899dbb
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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