Hydrochloric Acid → Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylate

HRID 1050965Notes

Reaction equation

HRID 1050965 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](OC)=[O:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([SiH2]CC)C.Cl>ClCCl.C1CCCC=CCC1.C1CCCC=CCC1.C1CCCC=CCC1.C1CCCC=CCC1.[Cl-].[Cl-].[Ir].[Ir]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([CH:20]=[O:21])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68337DiethylsilaneHCID 22492933Tert-butyl 4-[4-(methoxycarbonyl)phenyl]-1-piperidinecarboxylate

Product 1

HCID 11254770Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 91972094Chlorobis(cyclooctene)iridium(I) dimerCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (776 mg, 2.43 mmol) in dichloromethane (10 ml) are added diethylsilane (470 μl, 3.64 mmol) and chlorobis(cyclooctene)iridium(I) dimer (22 mg, 0.025 mmol) and the mixture is irradiated in a microwave reactor for 1.5 hours at 50° C. The reaction mixture is stirred vigorously with 2 N hydrochloric acid (0.6 ml) for 30 minutes. The organic layer is separated, dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 4-(4-formyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester as yellow resin; HPLC/MS 2.10 min (A), [M-tBu] 234.

Workup

  1. customthe mixture is irradiated in a microwave reactor for 1.5 hours at 50° C
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-a2d39eaebcff4592a102c56034108187
Source dataset
uspto-grants-2016_07
Patent number
US09388142B2

Reaction notes

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