Hydrochloric Acid → HCID 58109700, compound

HRID 2037588Notes

Reaction equation

HRID 2037588 reaction equation
[CH2:1]([C@@:4]1([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:35]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[CH2:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@H:11]([N:7]2[CH2:6][CH2:5][C@@:4]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)([CH2:1][CH2:2][CH2:3][OH:35])[O:9][C:8]2=[O:10])[CH2:12]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 58109649HCID 58109649, compound

Product 1

HCID 58109700HCID 58109700, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-6-allyl-3-((S)-1-benzylpiperidin-3-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (90 mg, 0.22 mmol) in THF (3 mL) was added BH3/THF (1 M, 0.44 mL) at 0° C. and the mixture was stirred at rt for 2 h. Then the mixture was cooled at 0° C., and H2O (0.2 ml), NaOH (3 M, 0.15 mL), 30% H2O2 (0.4 mL) were added. After the solution was stirred at rt for another 2 h, 1N aq HCl was added, and the mixture was extracted with EtOAc. The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparative TLC to give (R)-3-((S)-1-benzylpiperidin-3-yl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (30 mg, 30%). LC-MS Method 2 tR=0.976 min, m/z=427.7; 1H NMR (CDCl3): 1.28 (m, 2H), 1.36-1.45 (m, 1H), 1.58-1.67 (m, 6H), 1.88 (m, 2H), 2.10 (m, 1H), 2.17 (m, 1H), 2.48 (m, 1H), 2.64 (m, 2H), 3.12 (m, 1H), 3.34 (s, 2H), 3.48 (m, 2H), 4.05-4.15 (m, 1H), 6.94 (m, 2H), 7.15 (m, 5H), 7.22 (m, 2H).

Workup

  1. temperatureThen the mixture was cooled at 0° C.
  2. stirringAfter the solution was stirred at rt for another 2 h
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-4cf87f55a93e45ceb1ab4afa433131d6
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…