Water → tert-Butyl 4-sulfanylpiperidine-1-carboxylate

HRID 404741Notes

Reaction equation

HRID 404741 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14]C(=O)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([SH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 4311764Sodium borohydrideHCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

Product 1

HCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylateYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.15 g 4-Acetylsulfanyl-piperidine-1-carboxylic acid tert-butyl ester (272) were dissolved in 84 ml MeOH and treated with 2.1 g (55.5 mmol) sodium borohydride at 0° C. after stirring for 2 h at RT all volatiles were removed in vacuo and to the residue was added slowly water and 2.3 g (11 mmol) citric acid monohydrate. Extraction with dichloromethane, drying with Sodium sulfate and evaporation gave 1.78 g of crude 4-Mercapto-piperidine-1-carboxylic acid tert-butyl ester

Workup

  1. customwere removed in vacuo and to the residue
  2. extractionExtraction with dichloromethane
  3. dry with materialdrying with Sodium sulfate and evaporation

Sources & evidence

ORD record
ord-0d6a642b236646698391dbbdf1146283
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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