phosphoric acid dibenzyl ester (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester → phosphoric acid mono-{(3S,4 S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl} ester

HRID 2187095Notes

Reaction equation

HRID 2187095 reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][P:26](=[O:43])([O:35]CC3C=CC=CC=3)[O:27]CC3C=CC=CC=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O>[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([O:25][P:26](=[O:27])([OH:35])[OH:43])=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86584795phosphoric acid dibenzyl ester (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester

Product 1

HCID 10226177phosphoric acid mono-{(3S,4 S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl} esterYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.20 g, (1.73 mmol) phosphoric acid dibenzyl ester (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester in 40 ml MeOH and 6 ml water was hydrogenated at room temperature (20 bar, 5 h). The reaction mixture was concentrated to 20 ml and 500 ml water were added. The reaction mixture was filtered and the catalyst was washed with water. The filtrate was concentrated under reduced pressure until the product precipitates. The mixture was then cooled to 0° C. and 200 ml MeOH were added dropwise. After two hours the solid was filtered, washed with cold MeOH and dried at 60° C. under high vacuum to give 380 mg (0.83 mmol, 48%) of phosphoric acid mono-{(3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl} ester as colorless crystalls.

Workup

  1. customwas hydrogenated at room temperature
  2. custom(20 bar, 5 h)
  3. concentrationThe reaction mixture was concentrated to 20 ml and 500 ml water
  4. additionwere added
  5. filtrationThe reaction mixture was filtered
  6. washthe catalyst was washed with water
  7. concentrationThe filtrate was concentrated under reduced pressure until the product
  8. customprecipitates
  9. addition200 ml MeOH were added dropwise
  10. filtrationAfter two hours the solid was filtered
  11. washwashed with cold MeOH
  12. customdried at 60° C. under high vacuum

Sources & evidence

ORD record
ord-21d1120906d04a4682e4084fc7b2ccfe
Source dataset
uspto-grants-2002_06
Patent number
US06407235B1

Reaction notes

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