Brucine → HCID 18594875, compound

HRID 1580234Notes

Reaction equation

HRID 1580234 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; λmax. 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-315da0e140ce4d62a8c5c3cf22356e2d
Source dataset
uspto-grants-1976_01
Patent number
US03932472

Reaction notes

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