Sodium hydride → HCID 55300387, compound

HRID 1966575Notes

Reaction equation

HRID 1966575 reaction equation
C([O:8][C:9](=[O:17])[NH:10][CH2:11][CH2:12][C:13](O)([CH3:15])[CH3:14])C1C=CC=CC=1.[H-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][C:13]1([CH3:14])[O:17][C:9](=[O:8])[NH:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57516740HCID 57516740, compound

Product 1

HCID 55300387HCID 55300387, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(11.6 g, 48.9 mmol) (3-Hydroxy-3-methyl-butyl)-carbamic acid benzyl ester (Example 72, step 1) was dissolved in THF (250 ml) and sodium hydride (60%, 5.2 g, 108 mmol, 2.2 equiv.) was added in portions. The mixture was stirred for 3 hours at room temperature. 5 ml saturated NaHCO3 solution was added carefully and the mixture was evaporated with isolute to dryness. The crude product was purified by flash chromatography by directly loading the residue onto a silica gel column and eluting with an ethyl acetate:methanol gradient 100:0 to 90:10. The desired 6,6-dimethyl-[1,3]oxazinan-2-one (3.2 g, 51% yield) was obtained as a yellow solid, MS: m/e=130.1 (M+H+).

Workup

  1. customthe mixture was evaporated with isolute to dryness
  2. customThe crude product was purified by flash chromatography
  3. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-059d12bb819741cf8f56756029b93553
Source dataset
uspto-grants-2013_04
Patent number
US08420661B2

Reaction notes

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