Benzyl chloroformate → HCID 68994352, compound

HRID 657130Notes

Reaction equation

HRID 657130 reaction equation
[Na+].[OH:2][C@H:3]1[CH2:8][NH:7][CH2:6][C@@H:5]([C:9]([O-:11])=[O:10])[CH2:4]1.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>[OH-].[Na+]>[OH:2][C@H:3]1[CH2:8][N:7]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:6][C@@H:5]([C:9]([OH:11])=[O:10])[CH2:4]1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 131729308HCID 131729308, compound

Product 1

HCID 68994352HCID 68994352, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To cis-(3RS,5RS)-5-hydroxy-3-piperidinecarboxylic acid sodium salt (5.2 g; 31.0 mmol) in 0.5 N NaOH (100 ml) was added benzyl chloroformate (7.0 ml; 50.0 mmol) and the reaction was allowed to stir at room temperature under N2 for 14 hours. The reaction was extracted with diethyl ether (2×50 ml), acidified with 6N HCl (pH=2) and extracted with EtOAc (4×100 ml). The combined organic extracts were dried with Na2SO4, the solvents were removed to provide the desired compound (6.2 g; 72%).

Workup

  1. extractionThe reaction was extracted with diethyl ether (2×50 ml)
  2. extractionextracted with EtOAc (4×100 ml)
  3. dry with materialThe combined organic extracts were dried with Na2SO4
  4. customthe solvents were removed

Sources & evidence

ORD record
ord-50f6c725e57244c188dd6bd74d491f0d
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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