Benzene → HCID 23452596, compound

HRID 2048971Notes

Reaction equation

HRID 2048971 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].CS(Cl)(=O)=O.CS(C)=O.[BH4-].[Na+].[CH:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH:1]([N:3]1[CH2:6][CH2:7][CH:4]1[CH2:5][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4311764Sodium borohydride

Product 1

HCID 23452596HCID 23452596, compound

Procedure

To a solution of 6.0 g of threo-1-benzhydryl-2-(α-hydroxybenzyl)-azetidine and 1.84 g of triethylamine in 100 ml of dry benzene, maintained below -10° C., add 2.08 g of methanesulfonyl chloride. Allow the stirred solution to stand at 6°-10° C. for 2 hours. Add to the mixture, 150 ml of dry dimethyl sulfoxide and 1.40 g of sodium borohydride. Stir at room temperature for 85 hours. Add ether and water, separate the resultant layers, and re-extract the aqueous layer with additional ether. Wash the combined organic phases successively with water and brine, dry over anhydrous sodium sulfate, and remove solvent in vacuo. Chromatograph the resultant oil on 275 g of silica gel, eluting with 1/20 (v/v) ethyl acetate-hexane, to obtain the analytically pure product of this example, m.p. 87.5°-89.5° C.

Workup

  1. customAdd ether and water, separate the resultant layers
  2. extractionre-extract the aqueous layer with additional ether
  3. washWash the combined organic phases successively with water and brine
  4. dry with materialdry over anhydrous sodium sulfate
  5. customremove solvent in vacuo
  6. washChromatograph the resultant oil on 275 g of silica gel, eluting with 1/20 (v/v) ethyl acetate-hexane
  7. customto obtain the analytically pure product of this example, m.p. 87.5°-89.5° C.

Sources & evidence

ORD record
ord-83f013dfacd645d9803fb4a06aa6b403
Source dataset
uspto-grants-1980_04
Patent number
US04196124

Reaction notes

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