Triethylamine → (S)-6-phenyl-3-m-tolyl-1,3-oxazinan-2-one

HRID 1907258Notes

Reaction equation

HRID 1907258 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][CH2:8][CH2:9][C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[OH:11])[CH:2]=1.C(N(CC)CC)C.[C:26](=O)(OC(Cl)(Cl)Cl)[O:27]C(Cl)(Cl)Cl>C(Cl)Cl>[C:12]1([C@H:10]2[O:11][C:26](=[O:27])[N:7]([C:3]3[CH:2]=[C:1]([CH3:18])[CH:6]=[CH:5][CH:4]=3)[CH2:8][CH2:9]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 58200036(S)-3-(m-tolylamino)-1-phenylpropan-1-ol

Product 1

HCID 44231030(S)-6-phenyl-3-m-tolyl-1,3-oxazinan-2-oneYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(m-tolylamino)-1-phenylpropan-1-ol (40 mg, 0.17 mmol) in dry CH2Cl2 (1 mL) was added triethylamine (50 mg, 0.51 mmol) and bis(trichloromethyl) carbonate (20 mg, 0.067 mmol) at 0° C., and the reaction mixture was stirred overnight at room temperature. When the reaction was over, the mixture was concentrated to give the crude product, which was purified by preparative TLC (3:1 Petroleum ether/EtOAc) to give (S)-6-phenyl-3-m-tolyl-1,3-oxazinan-2-one (12 mg, 26%). 1H NMR: (400 MHz, CDCl3): δ=2.24-2.37 (m, 5H), 3.52-3.63 (m, 1H), 3.70-3.79 (m, 1H), 5.42 (dd, 1H), 7.01-7.10 (m, 3H), 7.18-7.23 (m, 2H), 7.32-7.39 (m, 4H).

Workup

  1. concentrationwas concentrated
  2. customto give the crude product, which
  3. customwas purified by preparative TLC (3:1 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-e414678c489c4bfe882e487173b3bdf6
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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