Water → HCID 13251127, compound

HRID 1912733Notes

Reaction equation

HRID 1912733 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCOC(C)=O.O>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:1][C@H:2]2[CH2:19][CH2:18][C@@:17]3([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]4[C@@H:16]3[CH2:15][CH2:14][C@@:12]3([CH3:13])[C@H:8]4[CH2:9][CH2:10][C:11]3=[O:21])[CH2:3]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5881DehydroepiandrosteroneHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl Acetate

Product 1

HCID 13251127HCID 13251127, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 3β-hydroxyandrost-5-en-17-one (10.00 g) in pyridine (66 mL), toluene-4-sulfonyl chloride (13.20 g) and DMAP (10 mg) were added at 0° C. under stirring. The reaction was allowed to warm to room temperature and stirred for 15 hr. After dilution with EtOAc (300 mL) the mixture was poured into iced water. The organic layer was separated, washed with 1N H2SO4, water and brine, dried and evaporated to dryness to give 3β-(p-toluensulfonyloxy)androst-5-en-17-one (14.70 g, 96%), as a white solid. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 7.81 (2H, m), 7.48 (2H, m), 5.35 (1H, m), 4.26 (1H, m), 2.46 (3H, s), 2.54-0.93 (19H, m), 1.05 (3H, s), 0.85 (3H, s).

Workup

  1. stirringstirred for 15 hr
  2. customThe organic layer was separated
  3. washwashed with 1N H2SO4, water and brine
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-cfe8272fc9fa45ea98b649f2831b98cb
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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