Benzyl Alcohol → 4-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

HRID 1901075Notes

Reaction equation

HRID 1901075 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([OH:14])=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:17]([O:13][C:12](=[O:14])[CH:11]1[CH2:15][CH2:16][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 222559134-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-t-butoxycarbonyl isonipecotic acid (12.0 g, 52.3 mmol) in 100 ml of anhydrous CH2Cl2, was added benzyl alcohol (6.0 ml, 58 mmol), followed by 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (11.04 g, 57.6 mmol), and 4-dimethylaminopyridine (642 mg, 5.25 mmol). The resulting mixture was stirred for 6 hours then diluted with CH2Cl2 (150 ml) and washed successively with H2O, 10% aqueous citric acid, saturated NaHCO3, brine and then dried over MgSO4. Concentration in vacuo afforded a colorless oil which was chromatographed on silica with 20% EtOAc/hexane as eluent. Appropriate fractions were combined and concentrated in vacuo to afford the product as a white solid.

Workup

  1. washwashed successively with H2O, 10% aqueous citric acid, saturated NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. concentrationConcentration in vacuo
  4. customafforded a colorless oil which
  5. customwas chromatographed on silica with 20% EtOAc/hexane as eluent
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aefd019e88ab4ae6a2d6a4fdb62757d9
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

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