Benzene → 1-tert-Butyl 4-methyl 4-(4-chlorophenyl)piperidine-1,4-dicarboxylate

HRID 556950Notes

Reaction equation

HRID 556950 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:24][O:15][C:14]([C:11]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]1)=[O:16]

Participants

5

Reactant 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 248288571-(Tert-butoxycarbonyl)-4-(4-chlorophenyl)piperidine-4-carboxylic acid

Product 1

HCID 497602451-tert-Butyl 4-methyl 4-(4-chlorophenyl)piperidine-1,4-dicarboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred 4-(4-chloro-phenyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (852 mg, 2.5 mmol) in methanol (5 ml)-benzene (17.5 ml) was added 15 ml (trimethylsilyl)diazomethane (2.0 M solution in hexanes) at room temperature. The mixture was stirred for 16 hours at room temperature and concentrated in vacuo. The residual yellow oil was purified by silica gel chromatography eluting with hexane-ethyl:acetate (9:1) to give the corresponding ester (780 mg, 88%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residual yellow oil was purified by silica gel chromatography
  3. washeluting with hexane-ethyl:acetate (9:1)

Sources & evidence

ORD record
ord-ae8065702e844b7084eedc41639c9680
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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