Hydrochloric Acid → HCID 59268893, compound

HRID 2061596Notes

Reaction equation

HRID 2061596 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:20]3[CH2:21][CH:22]([C:24]4[O:28][N:27]=[C:26]([CH3:29])[N:25]=4)[CH2:23][CH:12]2[CH2:13][C:14]2([CH2:19]3)OCC[O:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:12]3[CH2:23][CH:22]([C:24]4[O:28][N:27]=[C:26]([CH3:29])[N:25]=4)[CH2:21][CH:20]2[CH2:19][C:14](=[O:15])[CH2:13]3)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59268898HCID 59268898, compound

Product 1

HCID 59268893HCID 59268893, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

9-[(4-Chlorophenyl)sulfonyl]-7-(3-methyl-1,2,4-oxadiazol-5-yl)spiro[9-azabicyclo[3.3.1]nonane-3,2′-[1,3]dioxolane] (51) (0.40 g, 0.916 mmol) was covered with HCl in dioxane (4 N, 2 mL). The reaction mixture was stirred at room temperature for 2 h after which it was diluted with EtOAc and washed with aqueous sodium hydroxide (1 N). The organic phase was dried (Na2SO4), filtered and concentrated under vacuum to yield 0.36 g (quant.) of 9-[(4-chlorophenyl)sulfonyl]-7-(3-methyl-1,2,4-oxadiazol-5-yl)-9-azabicyclo[3.3.1]nonan-3-one (52). MS (ESI) 396.1 (M+H).

Workup

  1. washwashed with aqueous sodium hydroxide (1 N)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0f76e8e49553469783d7fed13b1ac982
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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