Triphenylphosphine → ethyl (2'-oxo-6,7-dihydro-5H-spiro[indeno[5,6-b]furan-3,3'-indol]-1'(2'H)-yl)acetate

HRID 645177Notes

Reaction equation

HRID 645177 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][C:25]=2O)[CH2:22][CH2:21][CH2:20]3)([CH2:15][OH:16])[C:7]1=[O:27])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:15][O:16][C:25]3[CH:24]=[C:23]4[C:19](=[CH:18][C:17]2=3)[CH2:20][CH2:21][CH2:22]4)[C:7]1=[O:27])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58872532ethyl [3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 59263405ethyl (2'-oxo-6,7-dihydro-5H-spiro[indeno[5,6-b]furan-3,3'-indol]-1'(2'H)-yl)acetateYield 16.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl[3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate (4.20 mmol) in anhydrous THF (60.0 mL) was added triphenylphosphine (1.43 g, 5.46 mmol) and diethyl azodicarboxylate (0.95 g, 5.46 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h and quenched with saturated ammonium chloride (20.0 mL). The mixture was extracted with ethyl acetate (3×50.0 mL). The combined organic layers was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (ethyl acetate/hexane, 1/4) to give the title compound (0.25 g, 16% in three steps): 1H NMR (300 MHz, CDCl3) δ 7.29 (td, 1H), 7.22-7.17 (m, 1H), 7.07 (t, 1H), 6.81 (s, 1H), 6.78 (d, 1H), 6.65 (s, 1H), 4.95 (d, 1H), 4.71 (d, 1H), 4.64 (d, 1H), 4.42 (d, 1H), 4.24 (q, 2H), 2.84 (t, 2H), 2.73-2.65 (m, 2H), 2.10-1.95 (m, 2H), 1.29 (t, 3H); MS (ES+) m/z 364 (M+1).

Workup

  1. customquenched with saturated ammonium chloride (20.0 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×50.0 mL)
  3. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-207614319a334d549b95891f827f0084
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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