Water → HCID 8027227, compound

HRID 1914574Notes

Reaction equation

HRID 1914574 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]2[NH:10][C:9](=O)[CH2:8]1.O>C1COCC1>[O:7]1[C@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]2[NH:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54519905HCID 54519905, compound

Product 1

HCID 8027227HCID 8027227, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

Lithium aluminium hydride (0.22 g, 5.79 mmol) was suspended in THF (2 mL) and to this was added a solution of cis-hexahydro-benzo[1,4]oxazin-3-one (0.224 g), 1.45 mmol) in THF (5 mL) under nitrogen. The mixture was heated at 80° C. for 2 hours and then allowed to cool before cautious addition of water. The resultant white suspension was filtered through Celite® then concentrated. The residue was applied to a 5 g SCX-2 cartridge, washed with methanol then eluted using 2 N ammonia in methanol to afford the title compound as a colourless oil (0.142 g). LCMS m/z 183.28 [M+H+MeCN]+ R.T.=0.37 min (Analytical Method 6).

Workup

  1. filtrationThe resultant white suspension was filtered through Celite®
  2. concentrationthen concentrated
  3. washwashed with methanol
  4. washthen eluted

Sources & evidence

ORD record
ord-6e676d2680704ca4bfe4ef4913afb0e0
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

Loading…