Acetyl chloride → HCID 66700959, compound

HRID 1253707Notes

Reaction equation

HRID 1253707 reaction equation
C([Cl:4])(=O)C.[N:5]12[CH2:12][CH2:11][CH:8]([CH2:9][CH2:10]1)[C@@H:7]([NH:13][C:14]([CH:16]1[CH2:29][CH2:28][C:19]3([CH2:24][CH2:23][N:22](C([O-])=O)[CH2:21][CH2:20]3)[CH2:18][CH2:17]1)=[O:15])[CH2:6]2>C(O)C>[ClH:4].[N:5]12[CH2:12][CH2:11][CH:8]([CH2:9][CH2:10]1)[C@@H:7]([NH:13][C:14]([CH:16]1[CH2:29][CH2:28][C:19]3([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[CH2:18][CH2:17]1)=[O:15])[CH2:6]2

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86645835HCID 86645835, compound

Product 1

HCID 66700959HCID 66700959, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (5 eq.) was added to an ice-cold solution of 9-((R)-quinuclidin-3-ylcarbamoyl)-3-azaspiro[5.5]undecane-3-carboxylate (0.271 mmol, 1 eq.) in ethanol. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue dissolved in acetone/ethanol (1:3, 3 ml) and diethyl ether (20 ml) was added. The white solid was filtered out, washed with diethyl ether and dried in vacuo. Yield: 86%

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in acetone/ethanol (1:3, 3 ml)
  3. additiondiethyl ether (20 ml) was added
  4. filtrationThe white solid was filtered out
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8a729c3fdb644be6b308e1434bae67fb
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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