Water → tert-Butyl 3-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

HRID 227264Notes

Reaction equation

HRID 227264 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28].O>CCO.C(Cl)Cl>[CH3:28][S:27][CH2:26][CH2:25][CH:24]1[NH:23][C:11]2([CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[NH:31][C:29]1=[O:30]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 18531008(2S)-2-amino-4-(methylsulfanyl)butanamide hydrochloride

Product 1

HCID 68838394tert-Butyl 3-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-tert-Butyloxycarbonylpiperidone (5.9 g, 29.8 mmol) and triethylamine (3.02 g, 29.8 mmol) were added to a solution of methioninamide hydrochloride (5.5 g, 29.8 mmol) in dry EtOH (66 ml), and the mixture was heated under reflux for 2.5 h. After addition of water (50 ml) and CH2Cl2 (200 ml), the organic phase was separated off, and the aqueous phase was extracted with CH2Cl2 (3×20 ml). The combined organic phases were dried over Na2SO4. After filtration, the solvent was removed by distillation. tert-Butyl 3-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate was obtained in a yield of 8.0 g (82% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. customthe organic phase was separated off
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×20 ml)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationAfter filtration
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-6ae4bf239cf74b64a8df3a14ca157885
Source dataset
uspto-grants-2009_07
Patent number
US07560468B2

Reaction notes

Loading…