Pyridine → 4-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid benzyl ester

HRID 618293Notes

Reaction equation

HRID 618293 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:25]([O:27][C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=2)=[O:26])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 543969734-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the alcohol (72.3 g, 0.31 moles) produced in Example 20 and pyridine (37.3 ml, 0.46 moles) in 300 ml of methylene chloride was added dropwise under nitrogen over two hours to a solution of 4-nitrophenyl chloroformate (92.8 g, 0.46 moles) in 600 ml of methylene chloride at room temperature. After the addition the reaction was stirred for two days at room temperature. The reaction was then extracted two times with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure. Recrystallization of the crude product from methylene chloride-diisopropyl ether gave the tide compound as a crystalline solid, mp 118-120° C.

Workup

  1. additionAfter the addition the reaction
  2. extractionThe reaction was then extracted two times with 1N HCl, multiple times with saturated Na2CO3
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customRecrystallization of the crude product from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-075352d6419a47da8663ccac75060e50
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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