HCID 68771630, compound → HCID 68770987, compound

HRID 1471367Notes

Reaction equation

HRID 1471367 reaction equation
[CH3:1][C@@H:2]1[CH:11]=[CH:10][CH2:9][C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[C@H:3]1[C:12](=[O:16])/[CH:13]=[CH:14]/[CH3:15]>C(O)C.[Pd]>[CH3:1][C@@H:2]1[CH2:11][CH2:10][CH2:9][C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[C@H:3]1[C:12](=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 68771630HCID 68771630, compound

Product 1

HCID 68770987HCID 68770987, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (E)-1-(rel-(6S,7R)-7-methylspiro[4.5]dec-8-en-6-yl)but-2-en-1-one (2.0 g, 9.16 mmol) in ethanol (30 ml) was treated with 10% Pd/C (0.4 g) and hydrogenated (20 bar) for 1.5 h. The resulting mixture was filtered and concentrated. FC (SiO2, hexane/MTBE 50:1) of the crude product (1.9 g) gave 1-(rel-(6S,7R)-7-methylspiro[4.5]decan-6-yl)butan-1-one (0.75 g, 37%). Boiling point: 95° C. (0.08 mbar).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-353b0560ef9b42eba58bbb766f9df46a
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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