tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 21993617, compound

HRID 1978325Notes

Reaction equation

HRID 1978325 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Cl:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O-].[Na+].CO>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:19][C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=2[Cl:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2734112(2-Chlorobenzyl)triphenylphosphonium ChlorideHCID 23694274Sodium methanolate methanol

Product 1

HCID 21993617HCID 21993617, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 9.199 g (46.168 mM) of 1-(tert-butoxycarbonyl)-4-piperidone and 19.5 g (46.2 mM) of 2-chlorobenzyltriphenylphosphonium chloride in 50 ml of methanol was added 8.91 g (46.2 mM) of 28% sodium methoxide-methanol at room temperature and the mixture was refluxed for 36 hours. This reaction mixture was poured in water and extracted with 2 portions of ethyl acetate. The pooled organic layer was dried over Na2SO4 and the solvent was distilled off under reduced pressure. To the residue was added diethyl ether and the resulting precipitate (triphenylphosphine oxide) was filtered off and washed with diethyl ether. The filtrate and washes were combined and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 6/1) and crystallized from cold hexane to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed for 36 hours
  2. extractionextracted with 2 portions of ethyl acetate
  3. dry with materialThe pooled organic layer was dried over Na2SO4
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the residue was added diethyl ether
  6. filtrationthe resulting precipitate (triphenylphosphine oxide) was filtered off
  7. washwashed with diethyl ether
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 6/1)
  10. customcrystallized from cold hexane

Sources & evidence

ORD record
ord-53364d7c6e874553a0b9e48d3ba4fbfc
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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