4-Methylcyclohexanone → Methyl (3R)-8-methyl-1-thia-4-azaspiro[4.5]decane-3-carboxylate hydrochloride

HRID 279864

Reaction equation

HRID 279864 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][SH:8])[NH2:6].[CH3:10][CH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1>CO>[ClH:1].[CH3:10][CH:11]1[CH2:16][CH2:15][C:14]2([S:8][CH2:7][C@@H:5]([C:4]([O:3][CH3:2])=[O:9])[NH:6]2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 115254-MethylcyclohexanoneHCID 2733208L-Cysteine, methyl ester, hydrochloride

Product 1

HCID 86740772Methyl (3R)-8-methyl-1-thia-4-azaspiro[4.5]decane-3-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

34.3 g of L-cysteine methyl ester hydrochloride and 15.4 ml of 4-methylcyclohexanone are suspended in 70 ml of methanol and the suspension is refluxed for 3 hours. The suspension is concentrated to dryness under reduced pressure and the residue is recrystallized from isopropanol/methanol to give 25 g of colorless crystals of melting point 180° C.

Workup

  1. temperaturethe suspension is refluxed for 3 hours
  2. concentrationThe suspension is concentrated to dryness under reduced pressure
  3. customthe residue is recrystallized from isopropanol/methanol

Sources & evidence

ORD record
ord-8dfe6a8dff9f400ebc720d0b424d8c3a
Source dataset
uspto-grants-1986_05
Patent number
US04587250

Linked notes

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