Borane;tetrahydrofuran → HCID 66857639, compound

HRID 2037680Notes

Reaction equation

HRID 2037680 reaction equation
[CH2:1]([C@@:4]1([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:36]CC1>C1COCC1>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C@:4]2([CH2:1][CH2:2][CH2:3][OH:36])[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([F:23])([F:24])[F:22])=[CH:17][CH:18]=3)[CH3:12])[CH2:6][CH2:5]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 66857740HCID 66857740, compound

Product 1

HCID 66857639HCID 66857639, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-2-one (500 mg, 1.6 mmol) in THF (20 mL) was added BH3/THF (1 M, 3.2 mL) at 0° C. The mixture was stirred at rt for 2 h. The mixture was quenched with H2O (2.5 mL) at 0° C., then NaOH (3 M, 1.1 mL) and 30% H2O2 (2.5 mL) were added. After stirring at rt for another 2 h, 1N HCl was added to the mixture. 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)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-2-one (320 mg, 62%).

Workup

  1. customThe mixture was quenched with H2O (2.5 mL) at 0° C.
  2. additionNaOH (3 M, 1.1 mL) and 30% H2O2 (2.5 mL) were added
  3. stirringAfter stirring at rt for another 2 h
  4. addition1N HCl was added to the mixture
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-7f841c898eb748f4904cdc4b45b6335b
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…