Ethyl Acetate → HCID 12885306, compound

HRID 525363Notes

Reaction equation

HRID 525363 reaction equation
[OH:1][C:2]1([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)C(O)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1(P([N:32]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CCO[C:38](C)=[O:39]>C1(C)C=CC=CC=1.CCCCCC>[C:12]1([CH:8]2[C:2]3([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)[O:1][C:38](=[O:39])[NH:32]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 226204(1-hydroxycyclohexyl)(phenyl)acetic acid

Product 1

HCID 12885306HCID 12885306, 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-hydroxycyclohexyl)-2-phenylacetic acid (6.5 g, 28.14 mmole, 1 eq.) in toluene (100 mL) were added TEA (2.5 eq) and diphenyl phosphoryl azide (2 eq). The resulting mixture was then stirred at 120° C. for 12 hours. Reaction progress was monitored by TLC (TLC eluent: 30% EtOAc in hexane). The reaction mixture was then cooled and toluene was removed under reduced pressure to afford the product. 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[4.5]decan-2-one (2 g, 31%). 1H NMR (400 MHz, DMSO-d6) δ: 8.04 (s, 1H), 7.26-7.41 (m, 5H), 4.54 (s, 1H), 1.93-1.97 (m, 1H), 1.48-1.78 (m, 4H), 1.12-1.33 (m, 5H). m/z (ESI) 232.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-3a79d719e789438ca20d13cadd6fcac1
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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