Tetrabutylammonium Fluoride → HCID 67269775, compound

HRID 602470Notes

Reaction equation

HRID 602470 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][C@@H:11]1[CH2:10][C@@H:9]([OH:8])[CH2:13][N:12]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:27]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10621099HCID 10621099, compound

Product 1

HCID 67269775HCID 67269775, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-ethoxy-3-oxopropyl)pyrrolidine-1-carboxylate (500 mg, 1.2 mmol, step 1 of Example 8) in tetrahydrofuran (5 mL) was added tetrabutylammonium fluoride solution (1.0 M in tetrahydrofuran, 1.36 mL, 1.4 mmol) at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 6 h. The mixture was diluted with ethyl acetate (100 mL), washed with water (20 mL), brine (20 mL). The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (2:1) to give 338 mg (95%) of the title compound as a colorless oil.

Workup

  1. washwashed with water (20 mL), brine (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-95e1f46ef9fd48b9baecefd574ff6003
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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