Tetrahydrofuran toluene → Ethyl 4-(4-hydroxy-1-piperidyl)-4-methyl-piperidine-1-carboxylate

HRID 1642465Notes

Reaction equation

HRID 1642465 reaction equation
[C:1]([C:3]1([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1)#N.C[Mg+].[Br-].C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[OH:20][CH:17]1[CH2:18][CH2:19][N:14]([C:3]2([CH3:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 57619806Ethyl 4-cyano-4-(4-hydroxy-1-piperidyl)piperidine-1-carboxylateHCID 178418689HCID 178418689, compound

Product 1

HCID 57619818Ethyl 4-(4-hydroxy-1-piperidyl)-4-methyl-piperidine-1-carboxylateYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-cyano-4-(4-hydroxy-1-piperidyl)piperidine-1-carboxylate (2.45 g, 8.69 mmol) in THF (20 mL) was added a 1.4 M solution of MeMgBr in toluene/THF (18.6 mL, 26.1 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 (2×25 mL). The combined extracts were concentrated in vacuo to afford the title compound (1.54 g, 65%), which was used in the next step without further purification. MS (M+1): 271.26.

Workup

  1. customThe reaction was then quenched with saturated aqueous ammonium chloride
  2. extractionthe mixture was extracted with dichloromethane (2×25 mL)
  3. concentrationThe combined extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-d6f4eb0725dd49f28bcc43cf5affb39a
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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