Methanol → HCID 58109161, compound

HRID 2037483Notes

Reaction equation

HRID 2037483 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.[BH4-].[Na+].CO>C1COCC1>[OH:19][CH2:18][C:17]1[CH:22]=[CH:23][C:14]([C@@H:12]([N:8]2[CH2:7][CH2:6][C@:5]([CH2:4][CH2:3][CH2:2][OH:1])([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:10][C:9]2=[O:11])[CH3:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58109311HCID 58109311, compound

Product 1

HCID 58109161HCID 58109161, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((S)-1-((R)-6-(3-hydroxypropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)benzoate (60 mg, 0.25 mmol) in THF (5 mL) was added NaBH4 (48 mg, 1.25 mmol). The mixture was heated to reflux for 15 minutes. Then methanol (3 mL) was added. The mixture was heated to reflux overnight. The reaction was quenched with water, and the solvent was removed. The aqueous layer was extracted with EtOAc for 3 times. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give the crude product, which was purified by preparative TLC to give (R)-3-((S)-1-(4-(hydroxymethyl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (5 mg, 5%). LC-MS Method 2 tR=1.29, min, m/z=370, 392; 1H NMR (CDCl3): 1.33 (m, 1H), 1.45 (m, 3H), 1.64 (m, 1H), 1.90 (m, 2H), 2.11-2.24 (m, 2H), 2.81 (m, 1H), 3.50 (m, 2H), 4.52 (s, 2H), 5.58 (m, 1H), 6.82 (m, 2H), 7.03 (m, 2H), 7.25 (m, 5H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 minutes
  3. temperatureThe mixture was heated
  4. temperatureto reflux overnight
  5. customThe reaction was quenched with water
  6. customthe solvent was removed
  7. extractionThe aqueous layer was extracted with EtOAc for 3 times
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customto give the crude product, which
  12. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-1e00c924a9b64bbda964850f2cbd7d40
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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