HCID 18391989, compound → (R)-(3-Pyrrolidineoxy)tetrahydro-2H-pyran

HRID 618281Notes

Reaction equation

HRID 618281 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 18391989HCID 18391989, compound

Product 1

HCID 18392016(R)-(3-Pyrrolidineoxy)tetrahydro-2H-pyranYield 122.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-3-(R)-tetrahydropyranyloxypyrolidine(8.78 g, 27.3 mmol) and Pearlman's catalyst (3.50 g) in MeOH (100 ml) was stirred under hydrogen atmosphere at rt for 4 h. After removal of the catalyst by Celite filtration, the filtrate was concentrated to give 5.74 g of clear light brown oil. This was used for the next reaction without purification.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby Celite filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b67e295ffa9640e4ae17ec6300c093c3
Source dataset
uspto-grants-1999_09
Patent number
US05952369

Reaction notes

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