Methyl Ethyl Ketone → (1S,2S)-2-(3-Ketopyrrolidinyl)-1-[3-(Cyclohexyl)Propoxy]Cyclohexane Monohydrochloride

HRID 254279Notes

Reaction equation

HRID 254279 reaction equation
[ClH:1].[O:2]=[C:3]1[CH2:7][CH2:6][N:5]([C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]2[O:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:4]1.O1C2(CCN([C@H]3CCCC[C@@H]3OCCCC3CCCCC3)C2)OCC1.CC(=O)CC>Cl>[ClH:1].[O:2]=[C:3]1[CH2:7][CH2:6][N:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]2[O:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:4]1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 86638597(1S,2R)-2-(3-Ketopyrrolidinyl)-1-[3-(cyclohexyl)propoxy]cyclohexane monohydrochlorideHCID 86638598HCID 86638598, compound

Product 1

HCID 67152365(1S,2S)-2-(3-Ketopyrrolidinyl)-1-[3-(Cyclohexyl)Propoxy]Cyclohexane Monohydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(1R,2S)/(1S,2R)-2-(3-Ketopyrrolidinyl)-1-[3-(cyclohexyl)propoxy]cyclohexane monohydrochloride: (1R,2R)/(1S,2S)-2-[1,4-Dioxa-7-azaspiro[4.4]non-7-yl]-1-[3-(cyclohexyl)propoxy]cyclohexane (ii) in a mixture of 6M HCl aqueous solution-butanone (1:4, v/v, 100 mL) was refluxed for 16 hours. The cooled reaction mixture was concentrated in vacuo and the residual aqueous solution was diluted with water (˜50 mL). The acidic aqueous solution was extracted with diethyl ether (50 mL) and then with dichloromethane (3×50 mL). The dichloromethane extracts were dried over sodium sulfate and the solvent was evaporated in vacuo to provide the crude title compound. The hydrochloride salt was crystallized by triturating in a mixture of diethyl ether-hexanes (1:1, v/v, ˜200 mL) and then precipitated from a mixture of dichloromethane-diethyl ether-hexanes to yield 0.8 g of the title compound, having the elemental analysis indicated in Table 1.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionthe residual aqueous solution was diluted with water (˜50 mL)
  5. extractionThe acidic aqueous solution was extracted with diethyl ether (50 mL)
  6. dry with materialThe dichloromethane extracts were dried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customto provide the crude title compound
  9. customThe hydrochloride salt was crystallized
  10. customby triturating in a mixture of diethyl ether-hexanes (1:1, v/v, ˜200 mL)
  11. customprecipitated from a mixture of dichloromethane-diethyl ether-hexanes

Sources & evidence

ORD record
ord-8e8c1873a0924e4fad54f4e5ef7b3e0d
Source dataset
uspto-grants-2011_01
Patent number
US07875611B2

Reaction notes

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