Brucine → HCID 18594875, compound

HRID 2071342Notes

Reaction equation

HRID 2071342 reaction equation
[N:1]([CH:4]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:5][CH2:6][C@@H:7]1[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10](=[O:23])[CH2:9][CH2:8]1)=[N+]=[N-].COC1C=C2[C@@]34[C@@H]5C[C@H]6C(CN5CC3)=CCO[C@H]3CC(=O)N([C@H]4[C@@H]63)C2=CC=1OC>[Pd]>[NH2:1][CH:4]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:5][CH2:6][C@@H:7]1[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10](=[O:23])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 442021BrucineHCID 18594802HCID 18594802, compound

Product 1

HCID 18594875HCID 18594875, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A 1.06 g. sample of ethyl 15-azido-9-oxo-prostanoate (Example 110) is hydrogenated using 100 mg. of 5% palladium on carbon in 50 ml. absolute alcohol for 16 hours. The filtration of the catalyst and evaporation of the solvent affords an oil. Silica gel chromatography gives 604 mg. of oil; λ max. 2.95, 6.30 (brucine) and 5.72 μ (carbonyl groups).

Workup

  1. filtrationThe filtration of the catalyst and evaporation of the solvent
  2. customaffords an oil
  3. customSilica gel chromatography gives 604 mg

Sources & evidence

ORD record
ord-f60c3c552dfc4ed5aa1086a1177ae164
Source dataset
uspto-grants-1977_09
Patent number
US04046787

Reaction notes

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