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

HRID 2187094
Notes
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Reaction equation

HRID 2187094 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]([OH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](O)(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31].CN(C1C=CC=CN=1)C>C(Cl)Cl>[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][C:27](=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1110Succinic AcidHCID 218852-DimethylaminopyridineHCID 9885963(3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenol

Product 1

HCID 12043165succinic acid mono-{(3 S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl}esterYield 7.9%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 1.0 g (2.66 mmol) (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenol in 25 ml CH2Cl2 were added 320 mg (3.2 mmol) succinic acid and 390 mg (3.2 mmol) dimethylaminopyridine and the reaction mixture was refluxed for 20 hours. The reaction mixture was concentrated to 10 ml and was purified by chromatography over silica gel to give 100 mg (0.21 mmol, 7.4%) succinic acid mono-{(3S,4S)-4-[2-(4-benzyl -3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl} ester as colorless oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 20 hours
  2. concentrationThe reaction mixture was concentrated to 10 ml
  3. customwas purified by chromatography over silica gel

Sources & evidence

ORD record
ord-eec90b919b9b41e48fdcc69fac5c3b87
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06407235B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes