Sodium Hydroxide → t-butyl [N-benzyloxycarbonyl-4-piperidinyloxy]acetate

HRID 1379112Notes

Reaction equation

HRID 1379112 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[CH2:10]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([O:26][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:22][CH2:21]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 10066408t-butyl [N-benzyloxycarbonyl-4-piperidinyloxy]acetate

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

28 ml of t-butyl bromoacetate and 1.4 g of tetra-n-butylammonium hydrogen sulphate in 10 ml of water are added to a solution of 30.1 g of N-benzyloxycarbonyl-4-hydroxy-piperidine in 300 ml of toluene. Thereafter, a solution of 125 g of sodium hydroxide in 125 ml of water is added dropwise thereto. After stirring overnight, the organic extracts are separated, dried and concentrated. After drying there are obtained 34.1 g of N-benzyloxycarbonyl-4-[(t-butoxy carbonyl) methoxy]-piperidine, Rf =0.76 (ethyl acetate). MS (EI): 293 (M-C4H8)+.

Workup

  1. customthe organic extracts are separated
  2. customdried
  3. concentrationconcentrated
  4. customAfter drying there

Sources & evidence

ORD record
ord-34fdb6070f664ee19975d044fe6d4423
Source dataset
uspto-grants-1997_09
Patent number
US05670515

Reaction notes

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