HCID 131737023, compound → (S)-Tetrahydro-2H-pyran-3-carboxylic acid

HRID 58880Notes

Reaction equation

HRID 58880 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]([O:9]CC2C=CC=CC=2)=[O:8])[CH2:2]1>CO.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]([OH:9])=[O:8])[CH2:2]1

Participants

4

Reactant 1

HCID 131737023HCID 131737023, compound

Product 1

HCID 40430219(S)-Tetrahydro-2H-pyran-3-carboxylic acidYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%, 1 g) was added to a solution of (S)-benzyl tetrahydro-2H-pyran-3-carboxylate (1.1 g, 5 mmol) in MeOH (10 mL). The suspension was stirred under hydrogen atmosphere at ambient temperature for 2 h. The catalyst was filtered off and washed with MeOH (5 mL). The filtrate and washings were combined and concentrated to dryness to afford (S)-tetrahydro-2H-pyran-3-carboxylic acid (0.6 g, 92% yield). (R)-Tetrahydro-2H-pyran-3-carboxylic acid was made in a similar manner.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH (5 mL)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-72bbe6b7befb49f086c3e7c5fbd1cfa2
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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