Sodium Hydroxide → HCID 58807846, compound

HRID 560335Notes

Reaction equation

HRID 560335 reaction equation
[C:1]1([C@H:7]2[O:14][CH2:13][C@H:12]3[N:8]2[C:9](=O)[C@@H:10]2[CH2:15][C@@H:11]23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH2:7]([N:8]1[CH2:9][C@H:10]2[C@H:11]([CH2:15]2)[C@H:12]1[CH2:13][OH:14])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 10798720HCID 10798720, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 58807846HCID 58807846, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

At 0° C. a solution of (1aS,1bS,4R,5aR)-4-Phenyl-tetrahydro-3-oxa-4a-aza-cyclopropa[a]pentalen-5-one (13.9 mmol) in THF (15 mL) is added dropwise to a suspension of lithium aluminum hydride (20.9 mmol) in THF (14 mL) and the mixture is stirred at reflux for 1 h. After cooling to 0° C. water (0.80 mL), aq. NaOH solution (15%, 0.80 mL), THF (15 mL) and additional water (2.0 mL) are added with caution and the mixture is stirred vigorously for 2 h. Na2SO4 is added, the suspension is filtered through celite and the solvents are removed in vacuo to give the desired product. LC-MS (basic): tR=0.84 min; [M+H]+=204.4.

Workup

  1. temperatureat reflux for 1 h
  2. additionare added with caution
  3. stirringthe mixture is stirred vigorously for 2 h
  4. filtrationthe suspension is filtered through celite
  5. customthe solvents are removed in vacuo

Sources & evidence

ORD record
ord-ce45ee645bdb44c6a62af73ed2858226
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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