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

HRID 2422394Notes

Reaction equation

HRID 2422394 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 overnight at room temperature. Then 4 M sodium hydroxide solution was added slowly to the mixture until a pH of 10 was achieved. The mixture was extracted with diethyl ether (4×40 ml), the combined organic phases were dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (2.6 g) was purified by flash chromatography (260 g, 30×5.6 cm) with ethyl acetate/methanol (9:1). Yield: 1.06 g (47%), brown oil.

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 to small volume under vacuum
  4. customThe crude product (2.6 g) was purified by flash chromatography (260 g, 30×5.6 cm) with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-5fe226b265bc4a29a7b4722b3a2a1b04
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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