Water → HCID 46238961, compound

HRID 1485879Notes

Reaction equation

HRID 1485879 reaction equation
COC[O:4][C:5]1[CH:6]=[CH:7][C:8]2[C@@H:9]3[C@@H:17]([CH2:18][C:19](=O)[C:20]=2[CH:21]=1)[C@H:16]1[C@@:12]([CH3:27])([C@@H:13]([O:23]COC)[CH2:14][CH2:15]1)[CH2:11][CH2:10]3.CC(OI1(OC(C)=O)(OC(C)=O)[O:41][C:39](=O)[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34]C1=2)=O.O.[CH2:51](Cl)Cl>>[CH3:51][O:41][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][C@@H:19]1[CH2:18][C@@H:17]2[C@H:9]([CH2:10][CH2:11][C@@:12]3([CH3:27])[C@H:16]2[CH2:15][CH2:14][CH:13]3[OH:23])[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:21][C:20]1=2

Participants

4

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 86663324HCID 86663324, compound

Product 1

HCID 46238961HCID 46238961, compound

Procedure

(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-one—Dess-Martin Periodinane (9.46 g, 22.3 mmol) is added portionwise to a solution of the compound from b) (7.0 g, 18.6 mmol) in 300 mL of CH2Cl2. The resulting reaction mixture stirred at room temperature for 3 hours. The mixture is poured into water and the layers are separated. The aqueous layer is extracted with CH2Cl2, and the combined organic extracts are washed with brine, dried (Na2SO4), filtered, and evaporated in vacuo to give a gooey, brown solid. Purification by silica gel column chromatography (15%) EtOAc/Hex) affords the title compound as a pale yellow, viscous oil (6.0 g, 86%).

Workup

  1. customThe resulting reaction mixture
  2. customthe layers are separated
  3. extractionThe aqueous layer is extracted with CH2Cl2
  4. washthe combined organic extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give a gooey, brown solid
  9. customPurification by silica gel column chromatography (15%) EtOAc/Hex)

Sources & evidence

ORD record
ord-73aee826ddf947818d0a080326b193ee
Source dataset
uspto-grants-2016_08
Patent number
US09422324B2

Reaction notes

Loading…