Triphenylphosphine → HCID 10886037, compound

HRID 1741854Notes

Reaction equation

HRID 1741854 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[O:7])=[CH:4][CH:3]=1.[CH2:27]([C:31]1[CH:36]=[CH:35][C:34]([C@H:37](O)[CH2:38][CH2:39][CH3:40])=[CH:33][CH:32]=1)[CH:28]([CH3:30])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:27]([C:31]1[CH:32]=[CH:33][C:34]([C@@H:37]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([C:8]3[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]4[C:16]=3[CH:15]=[CH:14][CH:13]=[CH:12]4)=[O:7])=[CH:25][CH:26]=2)[CH2:38][CH2:39][CH3:40])=[CH:35][CH:36]=1)[CH:28]([CH3:30])[CH3:29]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11063606HCID 11063606, compoundHCID 11824313Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate

Product 1

HCID 10886037HCID 10886037, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a mixture of ethyl 4-[1-(4-hydroxybenzoyl)indolizin- 3-yl]butyrate (392 mg), (R)-1-(4-isobutylphenyl)butan-1-ol (230 mg) and triphenylphosphine (292 mg) in tetrahydrofuran (3 ml) and toluene (15 ml) was added diethyl azodicarboxylate (0.178 ml) at -20° C. under nitrogen atmosphere. After the mixture was stirred at -20° C. under nitrogen for 2.5 hours, acetic acid (0.05 ml) was added and the mixture was warmed up to room temperature. The solvent was evaporated under reduced pressure and the residue was poured into a mixture of ethyl acetate and water. The organic phase was separated, washed with water and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel column eluting with a mixture of n-hexane and ethyl acetate (4:1) to give ethyl 4-[1-[4-[(S)-1-(4-isobutylphenyl)butoxy]benzoyl]indolizin-3-yl]butyrate (295 mg) as an oil.

Workup

  1. temperaturethe mixture was warmed up to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was poured into a mixture of ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel column
  9. washeluting with a mixture of n-hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-c9ae443382ea4d5a80d8cd5dab459ae9
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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