Sodium Hydroxide → 2-(2-Mercaptoethyl)-piperidine-1-carboxylic acid benzyl ester

HRID 1857643Notes

Reaction equation

HRID 1857643 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][S:19]C(=O)C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][SH:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 537924282-(2-Acetylsulfanylethyl)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 543726122-(2-Mercaptoethyl)-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-acetylsulfanylethyl)-piperidine-1-carboxylic acid benzyl ester (174 mg in 5.0 mL methanol) was added 2.16 mL of a 0.5N solution of sodium hydroxide and the mixture stirred at room temperature for 30 minutes. At this time the reaction was diluted with ethyl acetate and quenched by the addition of 0.1N hydrochloric acid. The organic portion was washed sequentially with 0.1N hydrochloric acid, water and brine then dried over magnesium sulfate. Concentration in vacuo gave the crude title compound.

Workup

  1. customquenched by the addition of 0.1N hydrochloric acid
  2. washThe organic portion was washed sequentially with 0.1N hydrochloric acid, water and brine
  3. dry with materialthen dried over magnesium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c76ad0babe2d40bd99e7b774a95b4539
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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