(R)-6-allyl-3-((S)-1-(4-(6-aminopyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one → 6-Phenyl-1,3-oxazinan-2-one

HRID 2037509Notes

Reaction equation

HRID 2037509 reaction equation
C([C@@:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:9][C:8](=[O:10])[N:7]([C@H](C2C=CC(C3C=NC(N)=CC=3)=CC=2)C)[CH2:6][CH2:5]1)C=C>O1CCCC1>[C:26]1([CH:4]2[O:9][C:8](=[O:10])[NH:7][CH2:6][CH2:5]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 1

HCID 59532384(R)-6-allyl-3-((S)-1-(4-(6-aminopyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 2410056-Phenyl-1,3-oxazinan-2-oneYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-6-allyl-3-((S)-1-(4-(6-aminopyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (90 mg, 0.23 mmol) in tetrahydrofuran (10 mL) was added BH3 THF (3.0 mL, 1 mol/L, 4 mmol) at 0° C. under nitrogen atmosphere. The formed mixture was stirred for 2 h. The reaction was quenched by water. Then NaOH (2 mL, 3 mol/L) and H2O2 (1 mL) was added to the above mixture. When the reaction was over, the mixture was extracted with EtOAc. The combined organic phase was concentrated to give the crude product, which was purified by preparative HPLC to give (R)-3-((S)-1-(4-(6-aminopyridin-3-yl)phenyl)ethyl)-6-3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (40 mg, 41%).

Workup

  1. customThe reaction was quenched by water
  2. additionThen NaOH (2 mL, 3 mol/L) and H2O2 (1 mL) was added to the above mixture
  3. extractionwas extracted with EtOAc
  4. concentrationThe combined organic phase was concentrated
  5. customto give the crude product, which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-281662fc59cc4ad2bc20b39abb67c50d
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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