Acetyl chloride → HCID 21955367, compound

HRID 2213042Notes

Reaction equation

HRID 2213042 reaction equation
C(Cl)(=O)C.[CH2:5]1[C:10]2([CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH2:9][CH2:8][CH2:7][O:6]1>CO>[CH2:5]1[C:10]2([CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[CH2:9][CH2:8][CH2:7][O:6]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 21955183tert-Butyl 2-oxa-9-azaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 21955367HCID 21955367, compoundYield 119.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (1 mL) was added to stirred, cooled (0° C.) methanol (10 mL) and the mixture was stirred at 0° C. for 5 minutes. 1,1-Dimethylethyl 2-oxa-9-azaspiro[5.5]undecane-9-carboxylate (Description 138, 78 mg, 0.27 mmol) was added and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, aqueous sodium carbonate (10%, 10 mL) was added and the mixture was extracted with dichloromethane (3×10 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound (50 mg, 100%). m/z (ES+) 156 (M+1).

Workup

  1. stirringthe mixture was stirred at 0° C. for 5 minutes
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. customThe solvent was evaporated under reduced pressure, aqueous sodium carbonate (10%, 10 mL)
  4. additionwas added
  5. extractionthe mixture was extracted with dichloromethane (3×10 mL)
  6. dry with materialThe combined organic fractions were dried (Na2SO4)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-814bd52efc5f4b43ba90b573fe34c479
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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