4-Toluenesulfonyl chloride → (20S)-1alpha,3beta-bis[(tetrahydro-2H-pyran-2-yl)oxy]-20-methyl-21-(p-toluenesulfonyloxy)pregn-5-ene

HRID 1105850Notes

Reaction equation

HRID 1105850 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[C@@:28]2([CH3:29])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:23])[CH2:21][OH:22])[CH2:11][C@@H:10]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:9]1.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[C@@:28]2([CH3:29])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:23])[CH2:21][O:22][S:44]([C:41]2[CH:42]=[CH:43][C:38]([CH3:48])=[CH:39][CH:40]=2)(=[O:46])=[O:45])[CH2:11][C@@H:10]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:9]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12851171(20S)-1alpha,3beta-bis[(tetrahydro-2H-pyran-2-yl)oxy]-20-methylpregn-5-en-21-ol

Product 1

HCID 12851153(20S)-1alpha,3beta-bis[(tetrahydro-2H-pyran-2-yl)oxy]-20-methyl-21-(p-toluenesulfonyloxy)pregn-5-eneYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a stirred solution of 3.7 g of (20S)-1α,3β-bis[(tetrahydro-2H-pyran-2-yl)oxy]-20-methylpregn-5-en-21-ol in 5 ml of pyridine at 0° was added a solution of 1.77 g of p-toluenesulfonyl chloride in 3 ml of pyridine dropwise over 10 min. After 165 min. at 0°, the mixture was poured into ice water and extracted with ether. The ether extract was washed with water, dried (Na2SO4) and evaporated under reduced pressure. The residue was dissolved in 100 ml of toluene, concentrated in a 50° bath at 11 mm and applied to 80 g of silica gel containing 1% pyridine. Elution with hexane--ether, 7:3, afforded 3.49 g (73%) of (20S)-1α,3β-bis[(tetrahydro-2H-pyran-2-yl)oxy]-20-methyl-21-(p-toluenesulfonyloxy)pregn-5-ene as a white amorphous solid.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved in 100 ml of toluene
  7. concentrationconcentrated in a 50° bath at 11 mm
  8. washElution with hexane

Sources & evidence

ORD record
ord-f7cd5407d88e42b98ed635f634d93d8a
Source dataset
uspto-grants-1982_01
Patent number
US04310467

Reaction notes

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