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

HRID 1599706Notes

Reaction equation

HRID 1599706 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-13785bc6389445848d05fa270dd9b07f
Source dataset
uspto-grants-1998_04
Patent number
US05741792

Reaction notes

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