Tetrabutylammonium Fluoride → HCID 59352744, compound

HRID 2385436Notes

Reaction equation

HRID 2385436 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([C:19]3[CH:20]=[CH:21][C:22]([O:24][Si](C(C)C)(C(C)C)C(C)C)=[CH:23][C:18]=3[O:17][CH2:16]2)[C:8]1=[O:35].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:24][C:22]1[CH:21]=[CH:20][C:19]2[C:9]3([CH2:16][O:17][C:18]=2[CH:23]=1)[C:10]1[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=1)[N:7]([CH2:6][C@H:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[C:8]3=[O:35]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 45280163HCID 45280163, compound

Product 1

HCID 59352744HCID 59352744, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1′-[(2R)-tetrahydrofuran-2-ylmethyl]-6-{[tris(1-methylethyl)silyl]oxy}spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.69 g, 3.43 mmol) in anhydrous tetrahydrofuran (15 mL) under nitrogen was added tetrabutylammonium fluoride (1 M solution in tetrahydrofuran, 10 mL, 10 mmol), and the mixture was stirred at ambient temperature for 16 h. The reaction mixture was concentrated, and the residue was re-dissolved in ethyl acetate (25 mL), washed with water (2×20 mL) and brine (20 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography with 40% ethyl acetate in hexanes to afford 6-hydroxy-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.00 g, 86%) as a colorless solid: mp 72-74° C.; 1H NMR (300 MHz, CDCl3) δ7.29 (ddd, J=7.5, 7.5, 1.2 Hz, 1H), 7.18-7.01 (m, 3H), 6.80-6.67 (br., 1H), 6.44 (d, J=8.4 Hz, 1H), 6.24 (d, J=2.1 Hz, 1H), 6.17-6.09 (m, 1H), 4.96-4.90 (m, 1H), 4.69-4.63 (m, 1H), 4.36-4.24 (m, 1H), 4.00-3.71 (m, 4H), 2.12-1.61 (m, 4H); MS (ES+) m/z 338.1 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was re-dissolved in ethyl acetate (25 mL)
  3. washwashed with water (2×20 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e4fa9956779548b598bb7dfe8642ca71
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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