Methyl chloroformate → Dimethyl 2-(4-tert-butylphenyl)piperidine-1,4-dicarboxylate

HRID 1963155Notes

Reaction equation

HRID 1963155 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][NH:13]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:34])[O:32][CH3:33]>ClCCl>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]2[C:31]([O:32][CH3:33])=[O:34])=[CH:8][CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731791Methyl 2-(4-tert-butylphenyl)piperidine-4-carboxylate hydrochloride

Product 1

HCID 66734603Dimethyl 2-(4-tert-butylphenyl)piperidine-1,4-dicarboxylateYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl 2-(4-tert-butylphenyl)piperidine-4-carboxylate hydrochloride (9.66 g, 30.98 mmol) in dichloromethane (100 mL) was added DIPEA (12 mL, 68.89 mmol). The reaction mixture was cooled in an ice-bath and methyl carbonochloridate (2.8 mL, 35.56 mmol) was added dropwise over 5 min. The reaction mixture was stirred for 18 h at room temperature and washed with 3.8 N HCl. The aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Dimethyl 2-(4-tert-butylphenyl)piperidine-1,4-dicarboxylate (10.6 g, quant.) was isolated as a dark brown oil. MS m/z 334 (M+H)+

Workup

  1. temperatureThe reaction mixture was cooled in an ice-bath
  2. washwashed with 3.8 N HCl
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-ec1d84f8161e4988a62df08f3ecffe10
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…