HCID 18780615, compound → HCID 18780625, compound

HRID 1421270Notes

Reaction equation

HRID 1421270 reaction equation
C([O:8][C:9]1[C:10]2[N:11]3[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24]CC4C=CC=CC=4)=[CH:20][CH:19]=1)[C:12]3=[CH:32][CH:33]=2)C1C=CC=CC=1>O1CCCC1.C(O)C.[Pd]>[OH:8][C:9]1[C:10]2[N:11]3[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[C:12]3=[CH:32][CH:33]=2

Participants

5

Reactant 1

HCID 18780615HCID 18780615, compound

Product 1

HCID 18780625HCID 18780625, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-benzyloxy-2-(4-benzyloxyphenyl)pyrrolo[2,1,5-cd]indolizine (48 mg, 0.11 mmol) in 2 ml of tetrahydrofuran and 3 ml of ethanol was hydrogenated in the presence of 10% palladium on carbon (30 mg). When the theoretical amount of hydrogen had been consumed the catalyst was filtered off and the filtrate was evaporated to afford 27 mg (99%) of the title compound. M.p. 165° C. (dec.). 1H-NMR (DMSO-d6, 200 MHz) δ: 6.92 (d, 2H), 7.15 (d, 1H), 7.36 (d, 1H), 7.43 (s, 1H), 7.73 (d, 1H), 7.88 (d, 2H). (Compound 53).

Workup

  1. customWhen the theoretical amount of hydrogen had been consumed the catalyst
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-23fa53a875c0428e8cfc572664216210
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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