HCID 278205, compound → HCID 118343089, compound

HRID 2202733Notes

Reaction equation

HRID 2202733 reaction equation
[O:1]=[C:2]1[CH:10]=[C:9]2[C:5]([C:11]([O:13][CH3:14])=[O:12])([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH2:3]1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>CCO>[O:1]=[C:2]1[CH2:10][C@@H:9]2[C@:5]([C:11]([O:13][CH3:14])=[O:12])([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH2:3]1.[O:1]=[C:2]1[CH2:10][C@H:9]2[C@:5]([C:11]([O:13][CH3:14])=[O:12])([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 278205HCID 278205, compoundHCID 493570Riboflavin

Product 2

HCID 118343030HCID 118343030, compoundYield 20.84%HCID 118343089HCID 118343089, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 6-oxo-2,3,3a,4,5,6-hexahydro-1H-indene-3a-carboxylate (1.32 g, 6.80 mmol) in EtOH (30 mL) was added palladium, 10 wt. %(dry basis) on activated carbon, wet, degussa type e101 ne/w (0.120 ml, 6.80 mmol) and the resulting mixture underwent hydrogenation using the hydrogenation kit for 3 h. The mixture was filtered through celite, concentrated and chromatographed on silica gel using 0-25% heptane/hexane to afford (3aS,7aR)-methyl 6-oxooctahydro-1H-indene-3a-carboxylate (0.278 g, 1.417 mmol, 20.84% yield) and (3aS,7aS)-methyl 6-oxooctahydro-1H-indene-3a-carboxylate (0.394 g, 2.008 mmol, 29.5% yield) as colorless oil. MS m/z=181.2 [M+H]+.

Workup

  1. dry with materialpalladium, 10 wt. %(dry basis) on activated carbon
  2. customfor 3 h
  3. filtrationThe mixture was filtered through celite,
  4. concentrationconcentrated
  5. customchromatographed on silica gel using 0-25% heptane/hexane

Sources & evidence

ORD record
ord-13123065f2914d33a68531a3622c3a44
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

Loading…