Carbon Dioxide → (4s)-2'-(3,3-Dimethylbutyl)-7'-(pyrimidin-5-yl)-5h-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335692Notes

Reaction equation

HRID 335692 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[N:23][CH:24]=4)=[CH:12][CH:13]=3)[C:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1.C(=O)=O>CO>[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[N:23][CH:24]=4)=[CH:12][CH:13]=3)[C@:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 58466165Racemic 2'-(3,3-dimethylbutyl)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Product 1

HCID 67242781(4s)-2'-(3,3-Dimethylbutyl)-7'-(pyrimidin-5-yl)-5h-spiro[oxazole-4,9'-xanthen]-2-amineYield 42.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic 2′-(3,3-dimethylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (490 mg) from step 1 was subjected to chromatography using 20:80:0.1 MeOH:CO2:DEA at 70 ml/min on a 20×150 mm ChiralPak AD-H column and 100-bar system pressure. The first peak (RT=1.97 min) provided (4S)-2′-(3,3-dimethylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (210 mg, 99% ee), and the second peak (RT=4.43 min) provided (4R)-2′-(3,3-dimethylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (>99% ee).

Sources & evidence

ORD record
ord-2afbed8d65104159a204f4b83bb64432
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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