HCID 70584169, compound → HCID 70585544, compound

HRID 1701451Notes

Reaction equation

HRID 1701451 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]([O:11][C@H:12]1[CH2:31][C@@:30]2([CH3:32])[C@@H:23]([CH2:24][CH:25]=[C:26]2[C:27](=[O:29])[CH3:28])[C@H:22]2[C@H:13]1[C@:14]1([CH3:34])[C@@H:19]([CH2:20][CH2:21]2)[CH2:18][C@@H:17]([OH:33])[CH2:16][CH2:15]1)=[O:10])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]>[Pd].C(OCC)(=O)C>[CH2:1]([N:4]([CH2:8][C:9]([O:11][C@H:12]1[CH2:31][C@@:30]2([CH3:32])[C@@H:23]([CH2:24][CH2:25][C@@H:26]2[C:27](=[O:29])[CH3:28])[C@H:22]2[C@H:13]1[C@:14]1([CH3:34])[C@@H:19]([CH2:20][CH2:21]2)[CH2:18][C@@H:17]([OH:33])[CH2:16][CH2:15]1)=[O:10])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 70584169HCID 70584169, compound

Product 1

HCID 70585544HCID 70585544, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

11β-N,N-Dipropylaminoacetoxy-3β-hydroxy-5α-pregn-16-en-20-one (150 mg) was stirred with 5% palladium on charcoal (100 mg) in ethyl acetate (25 ml) at 20° under hydrogen. After 1 hour the catalyst was separated off using a Kieselguhr filter aid and the ethyl acetate was evaporated to leave a white solid. This was recrystallised from ethyl acetate in petroleum ether to give title compound as white crystals, m.p. 145 to 147.5 [α]D +85.2°. (89 mg).

Workup

  1. customAfter 1 hour the catalyst was separated off
  2. filtrationfilter aid
  3. customthe ethyl acetate was evaporated
  4. customto leave a white solid
  5. customThis was recrystallised from ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-acf75827a6394c25a9b52f5f9b057073
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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