Water → HCID 67751231, compound

HRID 248843Notes

Reaction equation

HRID 248843 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH3:5].CS(O[CH2:11][CH2:12][S:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][C@H:19]2[CH2:22][C@@H:17]1[C:18]2([CH3:24])[CH3:23])(=O)=O.O>ClCCl>[CH3:23][C:18]1([CH3:24])[C@H:17]2[CH2:22][C@@H:19]1[CH2:20][CH2:21][C@H:16]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11][N:4]([CH2:3][CH2:2][OH:1])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 86746845HCID 86746845, compound

Product 1

HCID 67751231HCID 67751231, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

10 ml of N-(2-hydroxyethyl)-N-methylamine were added to the solution of 2-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethylthio]ethyl methanesulfonate in dichloromethane obtained above. The dichloromethane was then distilled off under reduced pressure, and the remaining reaction mixture was stirred at 60° C. for 4 hours. The reaction mixture was worked up by adding 30 ml of water and extracting the mixture with ethyl acetate. The organic phase was separated and concentrated. The remaining residue was purified by chromatography on silica gel using n-hexane/dichloromethane/methanol as the eluent. 2.6 g of N-(2-[2((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethy lthio]ethyl]-N-(2-hydroxyethyl)-N-methylamine were obtained.

Workup

  1. customobtained above
  2. distillationThe dichloromethane was then distilled off under reduced pressure
  3. customthe remaining reaction mixture
  4. extractionextracting the mixture with ethyl acetate
  5. customThe organic phase was separated
  6. concentrationconcentrated
  7. customThe remaining residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b40db4afaa2a4b2ab36ececccf60735a
Source dataset
uspto-grants-1993_05
Patent number
US05212173

Reaction notes

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