Hydrochloric Acid → 4-Butyl-4-(pyrrolidin-1-yl)cyclohexanone

HRID 1095489Notes

Reaction equation

HRID 1095489 reaction equation
O.Cl.[CH2:3]([C:7]1([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6].[OH-].[Na+]>CC(C)=O>[CH2:3]([C:7]1([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 574751141-(8-Butyl-1,4-dioxaspiro[4,5]dec-8-yl)pyrrolidine

Product 1

HCID 574751134-Butyl-4-(pyrrolidin-1-yl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Water (10.0 ml) and 37% hydrochloric acid (14.0 ml) were added to a solution of 1-(8-butyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine (2.70 g, 10.1 mmol) in acetone (100 ml) and the mixture was stirred at room temperature overnight. 4 M sodium hydroxide solution was then slowly added dropwise to the mixture until pH 10 was reached. The mixture was extracted with diethyl ether (4×40 ml) and the combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude produce (2.6 g) was purified by flash chromatography (260 g, 30×5.6 cm) with ethyl acetate/methanol (9:1).

Workup

  1. extractionThe mixture was extracted with diethyl ether (4×40 ml)
  2. dry with materialthe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated i
  4. customThe crude produce (2.6 g)
  5. customwas purified by flash chromatography (260 g, 30×5.6 cm) with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-8bfb23d7017a4cb2824764205f440bc4
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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