dibenzyl 2-hydroxy-2-isopropyl-3-(tetrahydro-2H-pyran-4-yl)succinate → 2-Hydroxy-2-isopropyl-3-(tetrahydropyran-4-yl)succinic acid

HRID 1774396Notes

Reaction equation

HRID 1774396 reaction equation
[OH:1][C:2]([CH:30]([CH3:32])[CH3:31])([CH:13]([CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[C:14]([O:16]CC1C=CC=CC=1)=[O:15])[C:3]([O:5]CC1C=CC=CC=1)=[O:4]>C(O)C.[Pd]>[OH:1][C:2]([CH:30]([CH3:32])[CH3:31])([CH:13]([CH:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)[C:14]([OH:16])=[O:15])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 66648508dibenzyl 2-hydroxy-2-isopropyl-3-(tetrahydro-2H-pyran-4-yl)succinate

Product 1

HCID 666488882-Hydroxy-2-isopropyl-3-(tetrahydropyran-4-yl)succinic acidYield 108.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of dibenzyl 2-hydroxy-2-isopropyl-3-(tetrahydro-2H-pyran-4-yl)succinate (112 mg, 0.255 mmol) in ethanol (2.8 mL) was added 10% palladium/carbon (44 mg, 50% wet), and the mixture was stirred under hydrogen stream at room temperature for 2 h. The catalyst was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure to give 72 mg (quantitative) of 2-hydroxy-2-isopropyl-3-(tetrahydropyran-4-yl)succinic acid as a foam.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2d635d6554a648829d7515b1f66fff70
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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