Sodium Bicarbonate → {1-[1-(4-Methoxy-phenyl)-4-oxo-cyclohexyl]-propyl}-carbamic acid benzyl ester

HRID 45195Notes

Reaction equation

HRID 45195 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH:11]([C:14]1([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH2:23][CH2:22][C:17]2(OCC[O:18]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CC(C)=O.Cl>[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH:11]([C:14]1([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH2:15][CH2:16][C:17](=[O:18])[CH2:22][CH2:23]1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58381001{1-[8-(4-Methoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-propyl}-carbamic acid benzyl ester

Product 1

HCID 58380957{1-[1-(4-Methoxy-phenyl)-4-oxo-cyclohexyl]-propyl}-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

534 mg of {1-[8-(4-Methoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-propyl}-carbamic acid benzyl ester (96) were dissolved in 1 mL of a 2:1 mixture of acetone and 6N aqueous hydrochloric acid. The reaction mixture was stirred for 16 h at room temperature, then dropped into 150 mL of saturated aqueous sodium bicarbonate solution. The phases were separated and the aqueous phase was extracted three times with dichloromethane (100 mL each). The combined organic phases were dried over magnesium sulphate, filtered and concentrated to give the ketone 97. Rt=1.58 min (Method 19). Detected mass: 396.3 (M+H+).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted three times with dichloromethane (100 mL each)
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-864f6d4d419e4a919ce777a0b90d09da
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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