Tetrabutylammonium Fluoride → HCID 117697875, compound

HRID 1778502Notes

Reaction equation

HRID 1778502 reaction equation
[Si]([O:8][CH2:9][C:10]1([CH2:34][O:35][Si](C(C)(C)C)(C)C)[CH2:14][CH2:13][CH:12]([CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[N:11]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])C)=[O:28])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[OH:8][CH2:9][C:10]12[N:11]([C:27]([O:29][CH:30]([CH3:32])[CH3:33])=[O:28])[CH:12]([CH2:13][CH2:14]1)[CH2:15][O:35][CH2:34]2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131734818HCID 131734818, compound

Product 1

HCID 117697875HCID 117697875, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl 2,2-bis[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(p-tolylsulfonyloxymethyl)pyrrolidine-1-carboxylate (410 mg, 0.64 mmol) and TBAF (1 M in THF, 4 mL) in THF (2 mL) was stirred at 50° C. for 16 h. Then the mixture was diluted with ethyl acetate (50 mL) and washed with saturated NH4Cl (50 mL) three times and water (50 mL) three times, dried over anhydrous sodium sulfate and concentrated in vacuo to afford isopropyl 5-(hydroxymethyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate 81j (73 mg, 47%) which was used for next step without further purification. MS: calc'd (MH+) 244, measured (MH+) 244.

Workup

  1. washwashed with saturated NH4Cl (50 mL) three times and water (50 mL) three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75dec2910dd44b9797525aa6b7c808dc
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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