HCID 11415922, compound → 3-Benzyl-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid

HRID 1369044Notes

Reaction equation

HRID 1369044 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC[C@@](CC2C=CC=CC=2)(C(O)=O)C1)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 11415922HCID 11415922, compoundHCID 40424117HCID 40424117, compound

Product 1

HCID 36954643-Benzyl-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid

Procedure

3-Benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester (76 g, 238 mmol) was dissolved in EtOAc (3,0 L) in a one neck flask (5 L) equipped with magnetic stirring. Then H2O (30 ml), R(+)-1-phenethylamine (18,2 ml, 143 mmol) and Et3N (13,2 ml, 95 mmol) were added and the mixture was stirred overnight at room temperature resulting in precipitation of white crystals (41,9 g), which were removed by filtration, washed with EtOAc and dried in vacuo. The precipitate was dissolved in a mixture of aqueous NaHSO4 (300 ml, 10%) and EtOAc (600 ml), layers were separated and the aqueous layer re-extracted with EtOAc (100 ml). The combined organic layers were washed with brine (100 ml), dried over MgSO4 and filtered. The solvent was removed in vacuo to afford a colorless oil, which was dissolved in EtOAc(1):heptane(10) and aged overnight. The crystals that had been formed were removed by filtration, washed with heptane and dried in vacuo to give one compound which is either (3R)-3-benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester or (3S)-3-benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester (27,8 g).

Workup

  1. customwere removed by filtration
  2. washwashed with EtOAc
  3. customdried in vacuo
  4. dissolutionThe precipitate was dissolved in a mixture of aqueous NaHSO4 (300 ml, 10%) and EtOAc (600 ml), layers
  5. customwere separated
  6. extractionthe aqueous layer re-extracted with EtOAc (100 ml)
  7. washThe combined organic layers were washed with brine (100 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent was removed in vacuo
  11. customto afford a colorless oil, which
  12. customThe crystals that had been formed
  13. customwere removed by filtration
  14. washwashed with heptane
  15. customdried in vacuo
  16. customto give one compound which

Sources & evidence

ORD record
ord-0b560bf53aaa4ff18c30f1eb1b6766b0
Source dataset
uspto-grants-2003_06
Patent number
US06576648B2

Reaction notes

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