Triphenylphosphine → (R)-6-(2-aminoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

HRID 403586Notes

Reaction equation

HRID 403586 reaction equation
[N:1]([CH2:4][CH2:5][C@@:6]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:14])[CH2:8][CH2:7]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH2:4][CH2:5][C@@:6]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]([CH3:18])([CH3:16])[CH3:17])[CH3:14])[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 58485263(S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

Product 1

HCID 58485270(R)-6-(2-aminoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-oneYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (219 mg, 0.63 mmol) in THF (5 mL) and H2O (0.25 mL) was added PPh3 (198 mg, 0.76 mmol), and the mixture was refluxed for 2 h. The solution was concentrated, and the residue was purified by preparative TLC to afford (R)-6-(2-aminoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (144 mg, 71%). 1H NMR (CDCl3): 0.61-0.69 (s, 9H), 1.02-1.08 (d, 3H), 1.98-2.14 (m, 3H), 2.23-2.31 (m, 1H), 2.48-2.56 (m, 1H), 2.58-2.67 (m, 1H), 2.77-2.86 (m, 1H), 3.07-3.12 (m, 1H), 4.33-4.40 (m, 1H), 6.98-7.04 (m, 2H), 7.21-7.24 (m, 2H).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-645e165666cd4af1ac05257b31b1adf8
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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