Tetrabutylammonium Fluoride → HCID 117653092, compound

HRID 713708Notes

Reaction equation

HRID 713708 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@H:13]([O:20][Si](C(C)(C)C)(C)C)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][C@H:9]1[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]([O:37][CH3:38])=[O:36])=[N:33][CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@H:13]([OH:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][C@H:9]1[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]([O:37][CH3:38])=[O:36])=[N:33][CH:34]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123935700HCID 123935700, compound

Product 1

HCID 117653092HCID 117653092, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylate (475 mg, 0.88 mmol) in THF (2.0 mL) was added 1.0M solution of TBAF in THF (5 mL, 5.0 mmol) and the resulting solution stirred for an 30 minutes at room temperature. The mixture was concentrate under vacuum and the residue taken up in dichloromethane (50 mL). The solution was washed with water (50 mL) and brine (50 mL). The organics were then dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified vial preparative TLC plate (2×1000 μM) eluting with 80% ethyl acetate in hexane to afford the title compound as a white foam (334 mg, 89%). LC-MS: C24H30N2O5 calculated 426.24 found m/z (ES) 427.2 (MH)+ and 327.2 (M-Boc)+.

Workup

  1. concentrationThe mixture was concentrate under vacuum
  2. washThe solution was washed with water (50 mL) and brine (50 mL)
  3. dry with materialThe organics were then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified vial preparative TLC plate (2×1000 μM)
  7. washeluting with 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d69bd60a9e5d4f658384cbc10ba850c6
Source dataset
uspto-grants-2015_11
Patent number
US09186354B2

Reaction notes

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