Water → HCID 59411603, compound

HRID 425795Notes

Reaction equation

HRID 425795 reaction equation
[CH3:1][CH:2]1[CH2:19][C@@H:5]2[C@@H:6]3[N:10]([C:11](=O)[C@@H:4]2[CH2:3]1)[C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:8][CH2:7]3.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.C(Cl)Cl.CO>[CH2:9]([N:10]1[CH2:11][C@H:4]2[C@H:5]([CH2:19][CH:2]([CH3:1])[CH2:3]2)[C@H:6]1[CH2:7][OH:8])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59411620HCID 59411620, compound

Product 1

HCID 59411603HCID 59411603, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of (1R,3aS,3bS,6aR)-5-methyl-1-phenyl-hexahydro-2-oxa-7a-aza-cyclopenta[a]pentalen-7-one (470 mg) in anh. THF (7 mL) was added LAH (160 mg, 2.3 eq) in small portion. The mixture then refluxed for 6 h before cooled to 0° C. To the reaction mixture were carefully added water (0.3 mL), aqueous NaOH solution (15%) (0.9 mL) and water (0.3 mL). The resulting solid was removed by filtration and the filtrate was concentrated in to yield a crude oil. FC (DCM/MeOH: 97/3 to 93/7) gave the title compound as a colourless oil.

Workup

  1. temperatureThe mixture then refluxed for 6 h
  2. customThe resulting solid was removed by filtration
  3. concentrationthe filtrate was concentrated in
  4. customto yield a crude oil

Sources & evidence

ORD record
ord-4123a07f9a76423784c71c4052f86f8d
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

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