HCID 54243088, compound → HCID 13519094, compound

HRID 652275Notes

Reaction equation

[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:29])[CH2:18][CH:19]2[CH2:27]Cl)[C:14](=[CH2:30])[CH2:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]>C1CCCCC=1.C(O)C.[Pd]>[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:29])[C@@H:18]4[CH2:27][C@@H:19]42)[C@@H:14]([CH3:30])[CH2:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 533 mg of 10% Pd/C in 31 ml of cyclohexene and 46 ml of ethanol is stirred for one hour at 80° C. bath temperature. To this mixture is added 7.5 g of 17-acetoxy-1-chloromethyl-6-methylene-4-pregnene-3,20-dione and the mixture is further stirred for 18 hours at 80° C. Subsequently the catalyst is suctioned off, washed with warm ethanol, and the filtrate is combined with 7 ml of concentrated hydrochloric acid. The mixture is concentrated to one-third of the reaction volume and poured on an ice water-sodium chloride solution. After the usual working-up step, the crude product is purified on 700 g of silica gel with a hexane-ethyl acetate gradient. Yield: 4.3 g of 17α-acetoxy-6α-methyl-1α,2α-methylene-4-pregnene-3,20-dione, mp 198°-200° C.

Workup

stirringthe mixture is further stirred for 18 hours at 80° C
washwashed with warm ethanol
concentrationThe mixture is concentrated to one-third of the reaction volume
additionpoured on an ice water-sodium chloride solution
customthe crude product is purified on 700 g of silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record: ord-253987a1ecf948c6b7f8ea1d4cfbb1c7
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04670427

Reaction notes

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