Dimethyl Sulfate → HCID 178493045, compound

HRID 478664Notes

Reaction equation

HRID 478664 reaction equation
[ClH:1].[CH:2]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:27][CH2:26][C:14]3([N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:17][CH2:16][CH:15]3[OH:25])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)([CH3:4])[CH3:3].[H-].[Na+].[CH3:30]OS(OC)(=O)=O>CN(C)C=O>[ClH:1].[CH:2]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:12][CH2:13][C:14]3([N:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:17][CH2:16][CH:15]3[O:25][CH3:30])[CH2:26][CH2:27]2)[CH2:7][CH2:6]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 178448105HCID 178448105, compound

Product 1

HCID 178493045HCID 178493045, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

RS)-8-(cis-4-Isopropyl-cyclohexyl)-1-phenyl-1,8-diaza-spiro[4.5]decan-4-ol hydrochloride (0.3 mmol) was dissolved in dimethylformamide (15 ml), sodium hydride (1.2 mmol) was added and the mixture stirred for 1 h at room temperature. Dimethylsulfate (0.9 mmol) was added and stirring continued for 5 h. The mixture was quenched with ice-water (10 ml) and saturated sodiumbicarbonate solution (10 ml) and extracted three times with dichloromethane. The organic phases were pooled, dried with Na2SO4 and concentrated. Chromatography on silica gel (ethyl acetate) yielded the desired product which was crystallized as its HCl-salt from ethanol. 55 mg (44%) (RS)-8-(cis-4-isopropyl-cyclohexyl)-4-methoxy-1-phenyl-1,8-diaza-spiro[4.5]decane hydrochloride (1:1) as a colorless solid, m.p. 214-215° C. and MS: m/e=371.4 (M+H+).

Workup

  1. stirringstirring
  2. waitcontinued for 5 h
  3. customThe mixture was quenched with ice-water (10 ml) and saturated sodiumbicarbonate solution (10 ml)
  4. extractionextracted three times with dichloromethane
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a1bc378c2ed3407b84aa0c917bb89aeb
Source dataset
uspto-grants-2003_11
Patent number
US06642247B2

Reaction notes

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