4-Toluenesulfonyl chloride → HCID 87938282, compound

HRID 585055Notes

Reaction equation

HRID 585055 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 20795049HCID 20795049, compound

Product 1

HCID 87938282HCID 87938282, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (6S)-(7,8-dihydro-6H-5-oxa-1-aza-phenanthren-6-yl)-methanol (0.14 g, 0.65 mmole) and p-toluenesulfonyl chloride (0.25 g, 1.3 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 0.23 g (96%) of the title compound as a solid, mp 123° C., [α]25D=+51.22° (4.92, 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-267eff8f608942d18ce957f1dbb5302e
Source dataset
uspto-grants-2005_08
Patent number
US06930109B2

Reaction notes

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