Hydrochloric Acid → 8-[(4-Methoxyphenyl)methyl]-9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane

HRID 73027Notes

Reaction equation

HRID 73027 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][O:25][C:12]3([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH2:11]2)=[CH:5][CH:4]=1.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][N:10]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][O:25][C:12]3([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[CH2:11]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70872472Tert-butyl 8-[(4-methoxyphenyl)methyl]-9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 708724608-[(4-Methoxyphenyl)methyl]-9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecaneYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 8-[(4-methoxyphenyl)methyl]-9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (500 mg, 1.11 mmol) in DCM (1 mL) was added HCl (3 mL of 4 M in dioxane, 11.05 mmol) dropwise. The reaction mixture was stirred overnight at room temperature. The solvent was concentrated in vacuo and the residue was dissolved in the minimum amount of DCM and precipitated with ether. The solvent was decanted and the residue was again washed with ether and dried to give 8-[(4-methoxyphenyl)methyl]-9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane (400 mg, 93%). ESI-MS m/z calc. 352.2. Found 353.7 (M+1)+; Retention time: 0.99 minutes (3 min run).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. dissolutionthe residue was dissolved in the minimum amount of DCM
  3. customprecipitated with ether
  4. customThe solvent was decanted
  5. washthe residue was again washed with ether
  6. customdried

Sources & evidence

ORD record
ord-20f949c0d9084a67864d13e9a48f83b0
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

Loading…