HCID 58109235, compound → HCID 58109535, compound

HRID 2037427Notes

Reaction equation

HRID 2037427 reaction equation
[CH3:1][C:2]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:7][C:6](=[O:8])[N:5]([C@H:9]([C:11]2[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=2)[O:14][CH2:15]C(OCC)=O)[CH3:10])[CH2:4][CH2:3]1.C[Mg]Br>C1COCC1>[OH:7][C:2]([CH3:3])([CH3:1])[CH2:15][O:14][C:13]1[CH:12]=[C:11]([C@@H:9]([N:5]2[CH2:4][CH2:3][C:2]([CH3:1])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:7][C:6]2=[O:8])[CH3:10])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 58109235HCID 58109235, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58109535HCID 58109535, compoundYield 150.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(3-((S)-1-((R/S)-6-methyl-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenoxy)acetate (0.0369 g, 0.0928 mmol) in THF (5 mL) was added methylmagnesium bromide (1.4 M in toluene/THF, 1.0 mL, 1.4 mmol) at rt under nitrogen. After stirring for 1 h, the mixture was quenched with saturated NH4Cl (1 mL), diluted with CH2Cl2, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford 0.0268 g (75%) of (R/S)-3-((S)-1-(3-(2-hydroxy-2-methylpropoxy)phenyl)ethyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one. LC-MS Method 1, tR=1.64 min, m/z=384 (M+1). 1H NMR (CDCl3) 7.41-7.23 (m, 6H), 6.92-6.88 (m, 2H), 6.84-6.81 (m, 1H), 5.77 (q, J=7.0 Hz, 1H), 3.78 (s, 2H), 2.70-2.67 (m, 2H), 2.29-2.24 (m, 1H), 2.23 (s, 1H), 2.06-1.98 (m, 1H), 1.64 (s, 3H), 1.35 (s, 6H), 1.27 (d, J=7.0 Hz, 3H).

Workup

  1. customthe mixture was quenched with saturated NH4Cl (1 mL)
  2. additiondiluted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customAfter the solvents were evaporated
  5. customthe residue was purified by chromatography on silica gel
  6. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-fe38c63138f243ae81e7b66b07ad2349
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…