Water → 1-Tert-butyl 4-chloromethyl piperidine-1,4-dicarboxylate

HRID 852340Notes

Reaction equation

HRID 852340 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C(=O)(O)[O-].[Na+].S(Cl)(O[CH2:27][Cl:28])(=O)=O>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:27][Cl:28])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 101075661-Tert-butyl 4-chloromethyl piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonyl-4-piperidyl-carboxylic acid (6.4 g) in dichloromethane (30 ml) was added water (30 ml), sodium bicarbonate (8.91 g) and tetrabutylammonium hydrogensulfate (0.95 g). The mixture was stirred at room temperature while chloromethyl chlorosulfate (3.19 ml) was added slowly. After stirring for a further 30 minutes the organic phase was separated and evaporated in vacuo. The crude product was distributed between diethyl ether and water. The organic phase was separated, dried and evaporated to yield the title compound as an oil.

Workup

  1. additionwas added slowly
  2. customwas separated
  3. customevaporated in vacuo
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-f27fe89dd7fb4024ab7e7a361a895337
Source dataset
uspto-grants-2007_08
Patent number
US07253193B2

Reaction notes

Loading…