Methyl iodide → 1-Boc-4-phenyl-4-piperidinedicarboxylic acid methyl ester

HRID 1682945Notes

Reaction equation

HRID 1682945 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[CH:25](N(CC)C(C)C)(C)C>C(#N)C.C(OCC)(=O)C>[CH3:25][O:15][C:14]([C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)=[O:16]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

Product 1

HCID 538083811-Boc-4-phenyl-4-piperidinedicarboxylic acid methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-tert-Butyloxycarbonyl-4-phenyl-piperidine-4-carboxylic acid (0.9162 g, 3 mmol) was allowed to react with methyl iodide (1.87 mL, 30 mmol, 10 eq.) in the presence of N,N-diisopropylethylamine (2.61 mL, 15 mmol, 5 eq.) in acetonitrile (30 mL) at 20° C. for 16 hours. The solution was diluted with ethyl acetate and washed with 1N HCl, saturated sodium bicarbonate and saturated sodium chloride. The organic phase was dried over magnesium sulfate and the solvent was concentrated in vacuo to give 0.935 g (98%) of the title compound.

Workup

  1. washwashed with 1N HCl, saturated sodium bicarbonate and saturated sodium chloride
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-785c90aa7ec443cbae151192ffcb4ff9
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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