HCID 58951536, compound → HCID 58951515, compound

HRID 2421224Notes

Reaction equation

HRID 2421224 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][O:9][C:10]([CH3:21])([CH2:18][CH:19]=[CH2:20])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1>C(OCC)(=O)C.[Pd]>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][O:9][C:10]([CH3:21])([CH2:18][CH2:19][CH3:20])[C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:3]1

Participants

4

Reactant 1

HCID 58951536HCID 58951536, compound

Product 1

HCID 58951515HCID 58951515, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.4 g of tert-butyl 2-((1R,3S)-3-hydroxycyclohexylmethoxy)-2-methylpent-4-enoate are issolved in 15 ml of ethyl acetate and, under an argon atmosphere in an autoclave, a patula tip of Pd/C (10%) is added. The autoclave is then flushed with H2, and the solution is stirred with an H2 pressure of 3 bar at RT overnight. The catalyst is then iltered off through Celite, and the filtrate is concentrated, resulting in 2.3 g of tert-butyl 2-((1R,3S)-3-hydroxycyclohexylmethoxy)-2-methylpentanoate as a mixture of two iastereomers as pale yellow oil.

Workup

  1. customThe autoclave is then flushed with H2
  2. concentrationthe filtrate is concentrated
  3. customresulting in 2.3 g of tert-butyl 2-((1R,3S)-3-hydroxycyclohexylmethoxy)-2-methylpentanoate as a mixture of two iastereomers as pale yellow oil

Sources & evidence

ORD record
ord-ea000268d10949b485c68f9eee4e2dc8
Source dataset
uspto-grants-2011_06
Patent number
US07956077B2

Reaction notes

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