(R)-2'-bromo-7'-(neopentyloxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine → (S)-2'-(neopentyloxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335773Notes

Reaction equation

HRID 335773 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:9][CH:10]=3)[C@:5]3([CH2:25][O:24][C:23]([NH2:26])=[N:22]3)[C:4]=2[CH:3]=1>[Pd].C(O)C>[CH2:17]([O:16][C:8]1[CH:9]=[CH:10][C:11]2[O:12][C:13]3[C:4](=[CH:3][CH:2]=[CH:15][CH:14]=3)[C@@:5]3([CH2:25][O:24][C:23]([NH2:26])=[N:22]3)[C:6]=2[CH:7]=1)[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 1

HCID 58466128(R)-2'-bromo-7'-(neopentyloxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Product 1

HCID 58466214(S)-2'-(neopentyloxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (R)-2′-bromo-7′-(neopentyloxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (0.0500 g, 0.120 mmol), ethanol (2 mL), and palladium 10% on activated carbon (0.013 g, 0.012 mmol) was stirred under 1 atm of H2 gas overnight. The catalyst was filtered through celite and the filtrate was concentrated in vacuo to provide (S)-2′-(neopentyloxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a white solid.

Workup

  1. filtrationThe catalyst was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c08d470b2438478183becacad6bc55c1
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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