4-Toluenesulfonyl chloride → HCID 87938230, compound

HRID 1070590Notes

Reaction equation

HRID 1070590 reaction equation
[N:1]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][CH2:9][C@H:8]([CH2:15][OH:16])[O:7]3)[CH:4]=[CH:3][CH:2]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[N:1]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][CH2:9][C@H:8]([CH2:15][O:16][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[O:7]3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 20795048HCID 20795048, compound

Product 1

HCID 87938230HCID 87938230, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (6R)-(7,8-dihydro-6H-5-oxa-1-aza-phenanthren-6-yl)-methanol (0.38 g, 1.8 mmole) and p-toluenesulfonyl chloride (0.67 g, 3.5 mmole) in anhydrous pyridine (50 mL) was allowed to stir for 24 hours and then the solvent was removed in vacuum. The residue was dissolved in ethyl acetate (50 mL) and washed with water (3×30 mL). The organic layer was dried over sodium sulfate and filtered, and the solvent was removed under vacuum. Column chromatography on silica gel (50% methylene chloride/hexane) afforded 0.62 g (95%) of the title compound as a solid, mp 123° C., [α]25D=−27.71° (c=5.0, CHCl3).

Workup

  1. customthe solvent was removed in vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with water (3×30 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-fd276bbece0e4f2996a70a8ba939b5f8
Source dataset
uspto-grants-2005_06
Patent number
US06903110B2

Reaction notes

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