Sodium Hydroxide → HCID 59645259, compound

HRID 600236Notes

Reaction equation

HRID 600236 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[N:13]=[CH:12][C:11]([CH:14]3[CH2:19][N:18]([CH2:20][CH2:21][CH3:22])[C:17](=O)[CH2:16][O:15]3)=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[N:13]=[CH:12][C:11]([CH:14]3[CH2:19][N:18]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:16][O:15]3)=[CH:10][CH:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59645264HCID 59645264, compound

Product 1

HCID 59645259HCID 59645259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the morpholin-3-one from example 42 (191 mg, 0.61 mmol) in dry THF (5 ml) was added lithium aluminium hydride (1M solution in diethyl ether) (1.25 ml, 0.61 mmol) and the reaction mixture was warmed to reflux for 2.5 hours. The reaction mixture was cooled to room temperature then 1M NaOH (1.25 ml) was added to give a white precipitate. The reaction mixture was filtered and concentrated in vacuo. The white solid was discarded. The concentrated filtrate was purified by column chromatography on silica eluting with dichloromethane:methanol (95:5) to give the title compound as a white film (108 mg, 0.36 mmol, 59%). 1H NMR (CDCl3, 400 MHz) δ: 0.92 (t, 3H), 1.61 (q, 2H), 2.10 (s, 6H), 2.15 (m 1H), 2.29 (dt, 1H), 2.40 (t, 2H), 2.82 (d, 1H), 3.02 (d, 1H), 3.90 (t, 1H), 4.08 (d, 1H), 4.71 (d, 1H), 5.89 (s, 2H), 7.20 (d, 1H), 7.81 (d, 1H), 8.60 (s, 1H). LRMS: m/z 300 (M-H+).

Workup

  1. temperaturethe reaction mixture was warmed
  2. temperatureto reflux for 2.5 hours
  3. customto give a white precipitate
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customThe concentrated filtrate was purified by column chromatography on silica eluting with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-e3290f59efb6455a98864c4e08ac4c4a
Source dataset
uspto-grants-2011_03
Patent number
US07902188B2

Reaction notes

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