Sodium hydride → HCID 58485274, compound

HRID 403594Notes

Reaction equation

HRID 403594 reaction equation
[C:1]([N:5]([CH2:10][CH2:11][C:12]([OH:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][CH:14]=[CH2:15])[C:6](=[O:9])OC)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>C1COCC1>[CH2:13]([C:12]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:22][C:6](=[O:9])[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11]1)[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58485261HCID 58485261, compound

Product 1

HCID 58485274HCID 58485274, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl tert-butyl(3-hydroxy-3-phenylhex-5-enyl)carbamate (600 mg, 1.97 mmol) in dry THF (10 mL) was added NaH (236 mg, 5.91 mmol) at 0° C. under N2, and the mixture was stirred at rt overnight. The reaction was quenched with water, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford the crude product, which was purified by preparative TLC to give 6-allyl-3-tert-butyl-6-phenyl-1,3-oxazinan-2-one (325 mg, 61%). 1H NMR (CDCl3): 1.23 (s, 9H), 2.01-2.21 (m, 1H), 2.28-2.34 (m, 1H), 2.45-2.59 (m, 2H), 2.71-2.81 (m, 1H), 3.13-3.21 (m, 1H), 4.92-5.02 (m, 2H), 5.53-5.63 (m, 1H), 7.21-7.34 (m, 5H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford the crude product, which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-0748199589724e758c3b29c4b27952c4
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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