HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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 1644480
Notes
Print preview

Reaction equation

HRID 1644480 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-29de0c101eba48f09005631571f5c528
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08124602B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes