Sodium Sulfite → 1-[(Benzyloxy)carbonyl]-3-piperidylmethanesulfonic acid

HRID 397679Notes

Reaction equation

HRID 397679 reaction equation
[S:1]([O-:4])([O-:3])=[O:2].[Na+].[Na+].Br[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1>O.O1CCOCC1>[CH2:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][CH:9]([CH2:8][S:1]([OH:4])(=[O:3])=[O:2])[CH2:10]1)=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 23000675Benzyl 3-(bromomethyl)piperidine-1-carboxylate

Product 1

HCID 545518421-[(Benzyloxy)carbonyl]-3-piperidylmethanesulfonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium sulphite (12.6 g) in water (25 ml) was added to a stirred solution of benzyl 3-(bromomethyl)-1-piperidinecarboxylate (7.8 g) [Preparation 60] in dioxan (25 ml). The reaction mixture was stirred at reflux for 18 hrs, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The aqueous solution was separated and acidified with 2N aqueous hydrochloric acid. The product was then extracted with ethyl acetate, dried over magnesium sulphate and the solvent removed under reduced pressure to afford 1-[(benzyloxy)carbonyl]-3-piperidylmethanesulfonic acid as a hygroscopic solid (4.5 g).

Workup

  1. temperatureat reflux for 18 hrs
  2. customafter which time the solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe aqueous solution was separated
  5. extractionThe product was then extracted with ethyl acetate
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-fa6fdf6b73094bc0ba5b0705675360cd
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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