HCID 10171428, compound → 2-[(4S)-2,2-Dimethyl-1,3-dioxan-4-yl]-2-methylheptan-3-one

HRID 736852Notes

Reaction equation

HRID 736852 reaction equation
[CH3:1][C:2]([C@@H:10]1[CH2:15][CH2:14][O:13][C:12]([CH3:17])([CH3:16])[O:11]1)([C:4](=[O:9])[CH2:5][CH2:6][CH:7]=[CH2:8])[CH3:3]>C1COCC1.[Pd]>[CH3:3][C:2]([C@@H:10]1[CH2:15][CH2:14][O:13][C:12]([CH3:16])([CH3:17])[O:11]1)([C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH3:1]

Participants

4

Reactant 1

HCID 10171428HCID 10171428, compound

Product 1

HCID 673878332-[(4S)-2,2-Dimethyl-1,3-dioxan-4-yl]-2-methylheptan-3-oneYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

24 g (0.1 mol) of (4S)-4-(2-methyl-3-oxo-hept-6-en-2-yl)-2,2-dimethyl-[1,3]dioxane from Example 17 is dissolved in 480 ml of THF. At room temperature, 4.8 g of palladium on carbon (10%) is added. It is hydrogenated at 10 bar of hydrogen for 2 hours until hydrogen absorption is completed. The catalyst is suctioned off, rewashed with THF, and the product is distilled at 95° C./1 mbar. 21 g of product (87% of theory) is obtained.

Workup

  1. customIt is hydrogenated at 10 bar of hydrogen for 2 hours until hydrogen absorption
  2. distillationthe product is distilled at 95° C./1 mbar

Sources & evidence

ORD record
ord-2da4f7788d3f43a2b009dcd467fcff67
Source dataset
uspto-grants-2009_09
Patent number
US07595418B2

Reaction notes

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