Ethyl Acetate → HCID 89813819, compound

HRID 525360Notes

Reaction equation

HRID 525360 reaction equation
[OH:1][C:2]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)C(O)=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.C1(P([N:31]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CCO[C:37](C)=[O:38]>C1(C)C=CC=CC=1.CCCCCC>[C:11]1([CH:7]2[C:2]3([CH2:3][CH2:4][CH2:5][CH2:6]3)[O:1][C:37](=[O:38])[NH:31]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 91332α-(1-Hydroxycyclopentyl)benzeneacetic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 89813819HCID 89813819, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

To a 100 mL round bottom flask charged with 2-(1-hydroxycyclopentyl)-2-phenylacetic acid (3.5 g, 16.13 mmol, 1 eq.) in toluene (70 mL) were added TEA (2.5 eq) and diphenyl phosphoryl azide (2 eq). The resulting mixture was stirred at 120° C. for 12 hours. Reaction progress was monitored by TLC (TLC eluent: 30% EtOAc in hexane). The reaction mixture was cooled and toluene was removed under reduced pressure. The product thus obtained was purified by column chromatography using silica gel and eluting with 10% EtOAc in hexane to afford 4-phenyl-1-oxa-3-azaspiro[4.4]nonan-2-one (2 g, 31%). 1H NMR (300 MHz, CDCl3) δ: 8.06 (s, 1H), 7.28-7.41 (m, 5H), 4.78 (s, 1H), 1.88-2.03 (m, 2H), 1.23-1.70 (m, 5H), 0.97-1.03 (m, 1H). m/z (ESI) 218.3 (M+H)+.

Workup

  1. customReaction progress
  2. temperatureThe reaction mixture was cooled
  3. customtoluene was removed under reduced pressure
  4. customThe product thus obtained
  5. customwas purified by column chromatography
  6. washeluting with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-f381332d90d84c61b00780218c54c8f6
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…