HCID 59268882, compound → HCID 59268902, compound

HRID 2061599Notes

Reaction equation

HRID 2061599 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]([O:26]CC)=O)[CH2:23][CH:12]2[CH2:13][C:14]2([CH2:19]3)[O:18][CH2:17][CH2:16][O:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:29][CH2:30][Mg+].[Br-]>CCOCC.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([OH:26])[CH2:30][CH2:29]4)[CH2:21][CH:20]2[CH2:19][C:14]2([CH2:13]3)[O:15][CH2:16][CH2:17][O:18]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 59268882HCID 59268882, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 59268902HCID 59268902, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 9-[(4-chlorophenyl)sulfonyl]spiro[9-azabicyclo[3.3.1]nonane-3,2′-[1,3]dioxolane]-7-carboxylate (50) (395 mg, 0.918 mmol) was dissolved in Et2O (2 mL) and the resulting solution was cooled to −78° C. Ti(O-i-Pr)4 was added followed by EtMgBr dropwise over 10 minutes. The reaction mixture was warmed to room temperature and stirred for 18 h. The resulting solution was diluted with EtOAc and washed with saturated aqueous NH4Cl. The organic phase was dried (Na2SO4), filtered, and concentrated to give 1-{9-[(4-chlorophenyl)sulfonyl]spiro[9-azabicyclo[3.3.1]nonane-3,2′-[1,3]dioxolan]-7-yl}cyclopropanol (55). MS (ESI) 414.1 (M+H).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. washwashed with saturated aqueous NH4Cl
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c99b5d11b9d24dc19358a2bfa87fed1a
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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