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Tetrabutylammonium Fluoride → tert-butyl (2R,5R)-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-5-hydroxypiperidine-1-carboxylate

HRID 255351
Notes
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Reaction equation

HRID 255351 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH2:22][CH2:23][N:24]2[C:29]3[CH:30]=[C:31]([C:34]#[N:35])[CH:32]=[CH:33][C:28]=3[O:27][CH2:26][C:25]2=[O:36])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[C:34]([C:31]1[CH:32]=[CH:33][C:28]2[O:27][CH2:26][C:25](=[O:36])[N:24]([CH2:23][CH2:22][C@H:12]3[CH2:11][CH2:10][C@@H:9]([OH:8])[CH2:14][N:13]3[C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[C:29]=2[CH:30]=1)#[N:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66774834tert-butyl (2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate2×

Product 1

HCID 66774129tert-butyl (2R,5R)-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-5-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate (Intermediate 186, 1.01 g) in THF (10 mL) was added tetrabutylammonium fluoride (TBAF) (4 mL). After 5 hours, the reaction was diluted with ethyl acetate, washed with NaHCO3 and brine, dried over sodium sulfate and concentrated. The crude reaction mixture was used without further purification in the next step.

Workup

  1. washwashed with NaHCO3 and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude reaction mixture
  5. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-bffc88d53a2a40f38797ad1e48b7fa5f
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07875715B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes