Benzyl chloroformate → (2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid

HRID 1954677

Reaction equation

HRID 1954677 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O1CCCC1.O>[N:1]1([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 736316Pipecolic acid, (+)-

Product 1

HCID 688346(2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

D-hPro-OH (5.0 g, 38.7 mmol) was dissolved in tetrahydrofuran (100 mL) and water (30 mL). The pH of the solution was adjusted to 9.5 with 2N NaOH and benzyl chloroformate (5.5 mL, 38.7 mmol) was added dropwise and the pH maintained at 9.5 with 2N NaOH. The reaction was stirred for an additional 1 hour at room temperature. The organic solvent was evaporated in vacuo, and diethyl ether (100 mL) and water (50 mL) were added to the residue. The aqueous layer was separated, the pH of the aqueous solution was adjusted to 2.8 with 3N HCl, and ethyl acetate (150 mL) was added. The organic layer was separated and dried (MgSO4) and the filtrate was concentrated in vacuo to give 9.6 g (95%) of a clear oil.

Workup

  1. additionwas added dropwise
  2. customThe organic solvent was evaporated in vacuo, and diethyl ether (100 mL) and water (50 mL)
  3. additionwere added to the residue
  4. customThe aqueous layer was separated
  5. additionwas added
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-562908c1f98b4860998d2ec81c0eb866
Source dataset
uspto-grants-2000_09
Patent number
US06124277

Linked notes

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