Potassium Hydroxide → (S)-4-[[[1-[(1,1-Dimethylethoxy)carbonyl]-2-pyrrolidinyl]methoxy]methyl]-1-piperidinecarboxylic acid, phenylmethyl ester

HRID 1080843Notes

Reaction equation

HRID 1080843 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[K+].S(O[CH2:28][CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[CH2:31][CH2:30]1)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C(C)=CC=CC=1>[CH3:5][C:4]([CH3:7])([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][O:11][CH2:28][CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36])[CH2:31][CH2:30]1)=[O:2])[CH3:6]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 643448(S)-(-)-N-Boc-prolinolHCID 218920784-(Toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 131719745(S)-4-[[[1-[(1,1-Dimethylethoxy)carbonyl]-2-pyrrolidinyl]methoxy]methyl]-1-piperidinecarboxylic acid, phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To BOC-L-prolinol (10 mmol) in xylene (10 mL) was added KOH (20 mmol), 4-tosyloxymethyl-N-carbobenzyloxy piperidine (11 mmol) and the reaction was heated to reflux for 3 hours. The reaction mixture was stirred at room temperature for 16 hours, quenched with NH4Cl, extracted with ethyl acetate and purified by column chromatography to provide the title ether.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customquenched with NH4Cl
  4. extractionextracted with ethyl acetate
  5. custompurified by column chromatography
  6. customto provide the title ether

Sources & evidence

ORD record
ord-736035f1e0ea49408516f1b7fa8f6088
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

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