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

tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 58441736, compound

HRID 2262146
Notes
Print preview

Reaction equation

HRID 2262146 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([Li])CCC.[C:22]([N:29]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>O1CCCC1>[C:25]([O:24][C:22]([N:29]1[CH2:34][CH2:33][C:32]([C:9]2[S:10][C:5]3[C:4]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[N:3][C:2]([Cl:1])=[N:7][C:6]=3[CH:8]=2)([OH:35])[CH2:31][CH2:30]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 58441736HCID 58441736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To solution of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 (1.22 g) in anhydrous tetrahydrofuran (20 ml) stirring at −78° C. was added 2.5M n-butyllithium in hexanes (2.3 mL). The reaction mixture was warmed gradually to −40° C. over 1 hour, cooled to −78° C., and 1-BOC-4-Piperidone (950 mg) was added. The reaction mixture was gradually warmed to room temperature and then left to stir for 2 hours, poured into ice/water and extracted into ethyl acetate. After the usual drying and evaporation of the solvent, the residue was purified by flash chromatography to give 4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperaturecooled to −78° C.
  2. temperatureThe reaction mixture was gradually warmed to room temperature
  3. waitleft
  4. extractionextracted into ethyl acetate
  5. customAfter the usual drying
  6. customevaporation of the solvent
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2e7c3b962849450aa29fdad661c7300c
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846929B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes