Acetic Anhydride → HCID 66910130, compound

HRID 910601Notes

Reaction equation

HRID 910601 reaction equation
[OH:1][C@@H:2]1[CH:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH2:18]2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.[CH3:23][C:24](OC(C)=O)=[O:25]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:24]([O:1][C@@H:2]1[CH:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH2:18]2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1)(=[O:25])[CH3:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 66910083HCID 66910083, compound

Product 1

HCID 66910130HCID 66910130, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of 6α-hydroxyandrostane-3,17-dione (4.90 g) in pyridine (10 mL) at 0° C., DMAP (94 mg) and Ac2O (4.55 mL) were added. After stirring overnight at room temperature, the solution was evaporated. The residue was treated with water and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give 6α-acetoxyandrostane-3,17-dione (5.57 g, 100%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.66 (m, 1H), 2.47-2.33 (m, 2H), 2.30-2.01 (m, 4H), 2.00 (s, 3H), 1.98-1.08 (m, 12H), 1.05 (s, 3H), 1.00 (m, 1H), 0.84 (m, 1H), 0.80 (s, 3H).

Workup

  1. customthe solution was evaporated
  2. additionThe residue was treated with water
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-2fddf77e5c8f49b4bf986b8368104ee4
Source dataset
uspto-grants-2011_09
Patent number
US08022203B2

Reaction notes

Loading…