Tetrabutylammonium Fluoride → HCID 86726791, compound

HRID 1499569Notes

Reaction equation

HRID 1499569 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([CH3:17])[C@@H:14]([O:18]C(C)(C)C(C)(C)C)[C@H:13]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([CH3:17])[C@@H:14]([OH:18])[C@H:13]([NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86726792HCID 86726792, compound

Product 1

HCID 86726791HCID 86726791, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Benzyl-(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1,1,2,2-tetramethylpropoxy)piperidine-1-carboxylate (1.88 g, 4.06 mmol) was dissolved in THF (20 mL) and a 1.0 M solution of tetra-n-butylammonium fluoride in THF (4.7 mL, 4.7 mmol) was added. The reaction mixture was stirred for 30 min. at room temperature and then diluted with EtOAc. The mixture was washed 2 times with brine, then dried and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 25-75% EtOAc in hexanes to give the sub-title compound as a white solid (1.48 g, 82%). LCMS calc. for C19H28N2NaO5 (M+Na)+ m/z=387.2. found 387.0.

Workup

  1. washThe mixture was washed 2 times with brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with 25-75% EtOAc in hexanes

Sources & evidence

ORD record
ord-18a6d85b15374319b423fb3e572bcdae
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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