Hydrochloric Acid → tert-Butyl 3-sulfanylpiperidine-1-carboxylate

HRID 468568Notes

Reaction equation

HRID 468568 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([S:14]C(=O)C)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[O-].[Na+].Cl>CO>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([SH:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 547762383-Acetylsulfanyl-1-Boc-piperidine

Product 1

HCID 49759132tert-Butyl 3-sulfanylpiperidine-1-carboxylateYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

200 g of N-BOC-3(R,S)-acetylthio-piperidine are placed in a 10 l reactor with 3.4 l of methanol in an inert atmosphere. To this solution 42 g of sodium methoxide in methanol is added over a period of 15 min. After additional stirring 170 ml of 5 n HCl are added, bringing the pH-value to 2.6-3. The solution is concentrated at an evaporator. The resulting biphasic mixture is taken up with 1.7 l of methyl tert.-butyl ether (MTBE) and 1.7 l of water. After shaking, separation of the aqueous phase and washing the MTBE phase is isolated and evaporated, yielding 170 g of an oil.

Workup

  1. additionare added
  2. concentrationThe solution is concentrated at an evaporator
  3. customseparation of the aqueous phase
  4. washwashing the MTBE phase
  5. customis isolated
  6. customevaporated

Sources & evidence

ORD record
ord-46f753999abb4c47a94701d90b42ecc9
Source dataset
uspto-grants-2014_01
Patent number
US08624033B2

Reaction notes

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