Tetrahydrofuran → HCID 18391709, compound

HRID 617346Notes

Reaction equation

HRID 617346 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH:16](O[Si](C(C)(C)C)(C)C)[O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C[O:53]CC1>>[C:1]([N:11]1[CH2:15][C@H:14]([OH:53])[CH2:13][C@H:12]1[CH2:16][O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 67586097HCID 67586097, compound

Product 1

HCID 18391709HCID 18391709, compound

Procedure

A 700 mg (1.6 mmol) sample of 3-(1-CBZ-(t-butyldimethylsilyloxy)-2-(S)-pyrrolidinylmethoxy)pyridine, prepared as in Example 72d above, was dissolved in 10 mL of THF and 5.0 mL (4.8 mmol) of 1 M tetra-n-butylammonium fluoride was added. The reaction mixture was stirred at room temperature for 2 hours, and the solvent was removed. The residue was purified on a column of silica gel, eluting with 3:1 ethyl acetate:hexane to give 466 mg of the title compound. MS (DCI/NH3) m/e: 328 (M+H)+. 1H NMR (CDCl3,300 MHz) δ: 8.28 (s, 1H), 8.21 (m, 1H), 7.33 (s, 5H), 7.27 (m, 1H), 7.20 (m, 1H), 5.13 (s, 2H), 4.59 (m, 1H), 4.37 (m, 1H), 3.62 (m, 2H), 3.59 (m, 1H), 3.20 (m, 1H), 2.18 (m, 1H).

Workup

  1. customthe solvent was removed
  2. customThe residue was purified on a column of silica gel
  3. washeluting with 3:1 ethyl acetate

Sources & evidence

ORD record
ord-09a7ada2a07644b1985138e68468ecbf
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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