Benzyl succinimido carbonate → 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

HRID 2354048Notes

Reaction equation

HRID 2354048 reaction equation
C1(C)C(S(O)(=O)=O)=CC=CC=1.[C:12]1([C:18]2([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:27]([O:34][C:35](ON1C(=O)CCC1=O)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:27]([O:34][C:35]([N:21]1[CH2:20][CH2:19][C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:24]([OH:26])=[O:25])[CH2:23][CH2:22]1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 86610990HCID 86610990, compound

Product 1

HCID 227417981-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of commercially available 4-phenyl-4-carboxypiperidine toluenesulfonate (7.55 g, 20 mmol), N-(benzyloxycarbonyloxy)succinimide (5.0 g, 20 mmol) and TEA (5 mL, 36 mmol) in CHCl3 (100 mL) is stirred at r.t. for 48 h. The mixture is diluted with CH2Cl2 (100 mL) and extracted with 1 M aq. NaOH (3×50 mL). The aq. phase is extracted with Et2O (2×50 mL), acidified (pH 2) with 6N aq. HCl and extracted with CH2Cl2 (4×50 mL). The combined CH2Cl2 extracts are dried (Na2SO4), filtered and evaporated to provide the title compound.

Workup

  1. extractionextracted with 1 M aq. NaOH (3×50 mL)
  2. extractionThe aq. phase is extracted with Et2O (2×50 mL)
  3. extractionextracted with CH2Cl2 (4×50 mL)
  4. dry with materialThe combined CH2Cl2 extracts are dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c3fd98c31da249ce9f49dfb94bca685a
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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