Benzene → HCID 23452596, compound

HRID 46457Notes

Reaction equation

HRID 46457 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-31808e45189b44df9804da04617a96f5
Source dataset
uspto-grants-1979_11
Patent number
US04173566

Reaction notes

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