Isopropanol → HCID 59352697, compound

HRID 1965695Notes

Reaction equation

HRID 1965695 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH:32]([OH:35])([CH3:34])[CH3:33].O[C:37]1[CH:42]=[CH:41][C:40]2[C:43]3([CH2:59][O:60][C:39]=2[CH:38]=1)[C:51]1[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=1)[N:45]([CH2:52][C@H:53]1[CH2:57][CH2:56][CH2:55][O:54]1)[C:44]3=[O:58]>>[CH3:33][CH:32]([O:35][C:37]1[CH:42]=[CH:41][C:40]2[C:43]3([CH2:59][O:60][C:39]=2[CH:38]=1)[C:51]1[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=1)[N:45]([CH2:52][C@H:53]1[CH2:57][CH2:56][CH2:55][O:54]1)[C:44]3=[O:58])[CH3:34]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59352744HCID 59352744, compound

Product 1

HCID 59352697HCID 59352697, compoundYield 85%

Procedure

To a stirred solution of triphenylphosphine (0.23 g, 0.89 mmol) in anhydrous tetrahydronfuran (200 mL) at 0° C. under nitrogen were added diethyl azodicarboxylate (0.14 mL, 0.89 mmol), isopropanol (0.23 mL, 2.97 mmol) and 6-hydroxy-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1H)-one (0.20 g, 0.59 mmol). The reaction mixture was stirred at ambient temperature for 16 h, and then the reaction was quenched with ammonium chloride solution. The solvent was removed, and the residue was dissolved in ethyl acetate (100 mL), which was washed with water, brine, dried over sodium sulfate and filtered. The filtrate was concentrated to dryness, and the residue was purified by flash chromatograph with 25% ethyl acetate in hexanes to afford 6-(1-methylethoxy)-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.19 g, 85%) as colorless liquid; 1H NMR (300 MHz, CDCl3) δ7.33-7.25 (m, 1H), 7.16-6.99 (m, 3H), 6.58 (d, J=8.4 Hz, 1H), 6.50 (d, J=1.8 Hz, 1H), 6.33 (dd, J=8.4, 2.1 Hz, 1H), 4.93 (d, J=9.0 Hz, 1H), 4.68 (d, J=9.0 Hz, 1H), 4.53-4.43 (m, 1H), 4.33-4.23 (m, 1H), 4.00-3.66 (m, 4H), 2.10-1.66 (m, 4H), 1.31 (d, J=6.0 Hz, 6H); MS (ES+) m/z 380.0 (M+1), 402.0 (M+23).

Workup

  1. customthe reaction was quenched with ammonium chloride solution
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  4. washwhich was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to dryness
  8. customthe residue was purified by flash chromatograph with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-975bb3e0bcce440984e43f34c1a7dcd3
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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