Tetrabutylammonium Fluoride → HCID 89851341, compound

HRID 627120Notes

Reaction equation

HRID 627120 reaction equation
[CH2:1]([O:4][N:5]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:6]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:9]([CH2:19][O:20][Si](C(C)(C)C)(C)C)[CH:8]=[C:7]1[CH2:28][O:29][CH3:30])[CH:2]=[CH2:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:4][N:5]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:6]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:9]([CH2:19][OH:20])[CH:8]=[C:7]1[CH2:28][O:29][CH3:30])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89852008(2S,5R)-tert-butyl 5-(allyloxy(tert-butoxycarbonyl)amino)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89851341HCID 89851341, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2S,5R)-tert-butyl 5-(allyloxy(tert-butoxycarbonyl)amino)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 71, 35.55 mmol) in THF (100 mL) at 0° C., TBAF (39.11 mL, 39.11 mmol) was added. After 1 hr at 0° C., it was then concentrated to give a residue which was purified by silica gel column (0-100% EA/Hex) to give the desired product (8.82 g, 57.9% over 3 steps) as a colorless oil.

Workup

  1. concentrationit was then concentrated
  2. customto give a residue which
  3. customwas purified by silica gel column (0-100% EA/Hex)

Sources & evidence

ORD record
ord-55df6dc9133d48098ec4ffc9a519fb4d
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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