(Oxan-4-yl)methanol → HCID 59551715, compound

HRID 1170244Notes

Reaction equation

HRID 1170244 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.CC([O-])(C)C.[K+].C(OC([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[C:37]3[C:32](=[CH:33][C:34](F)=[CH:35][CH:36]=3)[N:31]=[CH:30][N:29]=2)[CH2:24][CH2:23]1)=O)(C)(C)C>CS(C)=O.O>[NH:22]1[CH2:23][CH2:24][CH:25]([C:28]2[C:37]3[C:32](=[CH:33][C:34]([O:8][CH2:7][CH:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:35][CH:36]=3)[N:31]=[CH:30][N:29]=2)[CH2:26][CH2:27]1

Participants

6

Reactant 3

HCID 2773573(Oxan-4-yl)methanolHCID 23665647Potassium tert-butoxideHCID 595517364-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59551715HCID 59551715, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (tetrahydro-pyran-4-yl)-methanol (0.2 mmol), KOtBu (0.2 mmol) and 4-(7-fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.1 mmol), prepared as described in Example 12b, in DMSO (1 mL), was stirred at 80° C. for 1 h. It was then diluted with water and extracted with DCM. The combined extracts were washed with water, brine, dried with MgSO4, filtered, and concentrated in vacuo. The crude product was then treated with 3M HCl/MeOH (2 mL) and stirred at rt for 2 h and then concentrated in vacuo.

Workup

  1. customprepared
  2. extractionextracted with DCM
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe crude product was then treated with 3M HCl/MeOH (2 mL)
  8. stirringstirred at rt for 2 h
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-801b3a9953634567b5ef80c06ab8546e
Source dataset
uspto-grants-2010_11
Patent number
US07825244B2

Reaction notes

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