HCID 68952635, compound → (3R,6R,7aS)-6-(3-chloropropyl)-3-phenyl-dihydropyrrolo[1,2-c]oxazol-5(1H,3H,6H)-one

HRID 218434Notes

Reaction equation

HRID 218434 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1(C(O)=O)[C:18](=[O:19])[N:8]2[C@@H:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][CH2:11][C@@H:7]2[CH2:6]1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][C@H:5]1[C:18](=[O:19])[N:8]2[C@@H:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][CH2:11][C@@H:7]2[CH2:6]1

Participants

3

Reactant 1

HCID 68952635HCID 68952635, compound

Product 1

HCID 58011559(3R,6R,7aS)-6-(3-chloropropyl)-3-phenyl-dihydropyrrolo[1,2-c]oxazol-5(1H,3H,6H)-oneYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

The (3R,7aS)-6-(3-chloropropyl)-5-oxo-3-phenyl-hexahydropyrrolo[1,2-c]oxazole-6-carboxylic acid (32.65 g, 0.101 mol) was slurried in 300 mL of anhydrous toluene. The temperature of the mixture was raised to 120° C. over a ˜1 h period, and maintained at 120° C. for 2 h. After this time LC/MS analysis showed formation of the desired amide. The mixture was cooled to ambient temperature and transferred to a separatory funnel. The mixture was washed with 100 mL of half-saturated NaHCO3 solution and brine. During this process some insoluble material formed at the interface. This material was discarded. The toluene solution was stirred with 5 g of activated carbon (Norit, neutral) for 1 h, then filtered through a pad of Celite and evaporated. The amber syrup was placed on the vacuum line overnight. This afforded 26.7 g (94% yield) of (3R,6R,7aS)-6-(3-chloropropyl)-3-phenyl-dihydropyrrolo[1,2-c]oxazol-5(1H,3H,6H)-one.

Workup

  1. temperaturemaintained at 120° C. for 2 h
  2. temperatureThe mixture was cooled to ambient temperature
  3. customtransferred to a separatory funnel
  4. washThe mixture was washed with 100 mL of half-saturated NaHCO3 solution and brine
  5. customDuring this process some insoluble material formed at the interface
  6. filtrationfiltered through a pad of Celite
  7. customevaporated
  8. customwas placed on the vacuum line overnight

Sources & evidence

ORD record
ord-c9c280b1aa3d42af8b72dcef76d8d237
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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