(4S,5S)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol → (4S,5S)-5-amino-2,2-dimethyl-tetrahydropyran-4-ol

HRID 56439Notes

Reaction equation

HRID 56439 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][C@H:6]([OH:8])[C@@H:5]([NH:9][C@@H](C2C=CC=CC=2)C)[CH2:4][O:3]1.[H][H]>[Pd].CO>[NH2:9][C@H:5]1[CH2:4][O:3][C:2]([CH3:18])([CH3:1])[CH2:7][C@@H:6]1[OH:8]

Participants

5

Reactant 2

HCID 118036302(4S,5S)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 118036455(4S,5S)-5-amino-2,2-dimethyl-tetrahydropyran-4-olYield 189.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension mixture of (4S,5S)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol (1.0 g, 4.0 mmol) and 10% palladium on carbon (200 mg) in methanol (20 mL) was stirred at room temperature under 1 atm hydrogen atmosphere (hydrogen balloon) overnight. After that, the mixture was filtered through a pad of celite, and the filtrate was concentrated to get the title compound (1.1 g, crude) as a yellow oil, which was used directly for the next step without further purification.

Workup

  1. filtrationAfter that, the mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-05c2ba9f73e14c9a9e84c785b688f3ed
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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