Methanesulfonate → HCID 15390695, compound

HRID 651557Notes

Reaction equation

HRID 651557 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[OH:11].[Na].[C:13]1([CH:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:20]2[CH2:23][CH:22](OS(C)(=O)=O)[CH2:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S([O-])(=O)(=O)C>CC(C)CC(=O)C>[Cl:1][C:2]1[C:3]([O:11][CH:22]2[CH2:23][N:20]([CH:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:21]2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 85257MethanesulfonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 5360545SodiumHCID 15390710HCID 15390710, compound

Product 1

HCID 15390695HCID 15390695, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
120 °C

Procedure

2 g of 5-chloro-2,3-dihydro-1H-inden-4-ol were stirred in 75 ml of a 2N sodium hydroxyde solution for 1 hour. To the clear solution were added 75 ml of 4-methyl-2-pentanone and 3.76 g of 1-(diphenylmethyl)-3-methanesulfonyloxy-azetidine and the mixture was heated in an oil bath at 120° C. for 3.5 hours. Then another 2 g of mesylate were added and heating was continued for 64 hours. The upper layer was separated and washed with water. Evaporation in vacuo and chromatography with toluene/ethyl acetate (95:5) gave 4.22 g of 3-[(5-chloro-2,3-dihydro-1H-inden-4-yl)oxy]-1-(diphenylmethyl)-azetidine as a clear oil that solidified spontaneous. M.S. (C.I.) (M/Z): 391 [M+H]+.

Workup

  1. temperatureheating
  2. customThe upper layer was separated
  3. washwashed with water
  4. customEvaporation in vacuo and chromatography with toluene/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-00a6989cdd0e46edb8d682bbedc32cf3
Source dataset
uspto-grants-2001_08
Patent number
US06281243B1

Reaction notes

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