HCID 86735945, compound → HCID 86735946, compound

HRID 2419623Notes

Reaction equation

HRID 2419623 reaction equation
[CH3:1][O:2][C:3](=[O:35])/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][C@@H:26]2[O:29][CH:30]=[O:31])[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@H:19]([O:32][CH:33]=[O:34])[CH2:20][CH2:21]2)[CH2:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][C@@H:26]2[O:29][CH:30]=[O:31])[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@H:19]([O:32][CH:33]=[O:34])[CH2:20][CH2:21]2)[CH2:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9]

Participants

4

Reactant 1

HCID 86735945HCID 86735945, compound

Product 1

HCID 86735946HCID 86735946, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 g of 10% Pd/C and 7.6 g of 5-(3α,12α-diformyloxy-5β-pregnane-20-yl)-trans-2-pentenoic acid methyl ester in 100 ml of ethyl acetate was hydrogenated at atmospheric pressure. After completion of the reaction, the catalyst was filtered and the solvent removed under reduced pressure. Trituration of the residue with ether-hexane afforded 7.5 g of 5-(3α,12α-diformyloxy-5β-pregnane-20-yl)-pentanoic acid methyl ester mp 67-72°.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-706924eeacce4b4ca3b281b55718a3c9
Source dataset
uspto-grants-1978_08
Patent number
US04107188

Reaction notes

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