Borane;tetrahydrofuran → HCID 25182553, compound

HRID 2037422Notes

Reaction equation

HRID 2037422 reaction equation
[CH2:1]([C:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])[CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:35]CC1>C1COCC1>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N:7]2[CH2:6][CH2:5][C:4]([CH2:1][CH2:2][CH2:3][OH:35])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:9][C:8]2=[O:10])[CH:12]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 25182139HCID 25182139, compound

Product 1

HCID 25182553HCID 25182553, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 6-allyl-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (18 mg, 0.045 mmol) in THF (1 mL) was added BH3.THF (60 μL, 1M THF solution) and the mixture was stirred overnight at rt. The reaction was cooled to 0° C. and NaBO3.H2O (19 mg, 0.20 mmol) was added and stirred for 2 h warming to rt. The solvent was removed in vacuo and the residue was redissolved in CH3CN (4 mL). The solution was filtered and purified by prep HPLC to afford 3-(2′,4′-difluorobiphenyl-3-yl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (4.44 mg). LC-MS Method 1, tR=1.97 min, m/z=424 (M+H). 1H NMR (CDCl3) 7.47-7.33 (m), 7.32-7.26 (m), 7.16-7.12 (m), 6.96-6.85 (m), 4.28 (t), 3.52-3.13 (m), 3.36-3.27 (m), 2.5-2.47 (m), 2.15-1.99 (m).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringstirred for 2 h
  3. temperaturewarming to rt
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was redissolved in CH3CN (4 mL)
  6. filtrationThe solution was filtered
  7. custompurified by prep HPLC

Sources & evidence

ORD record
ord-a7c8a9bfa1dc4fc5a09a557329be3be6
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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