HCID 1070510, compound → HCID 16203557, compound

HRID 2189965Notes

Reaction equation

HRID 2189965 reaction equation
[C:1]([N:4]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C@@H:11]2[C:6]([C:7]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:8]=3[CH2:9][CH2:10]2)=[N:5]1)(=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:4]1[C@@H:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C@@H:11]2[C:6]([C:7]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:8]=3[CH2:9][CH2:10]2)=[N:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 1070510HCID 1070510, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 16203557HCID 16203557, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of (141) (180 mg, 0.51 mmol) in THF (5 mL) was added LiAlH4 (2.056 mL, 2.056 mmol; 1M in THF) at room temperature. The reaction mixture was stirred at room temperature for 1 h and then quenched with methanol followed by ice. The reaction mixture was extracted with ethyl acetate. Organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel using 25% ethyl acetate-hexane as eluent to give (157) (30 mg, 17%): thick oil, 1H NMR (500 MHz, CDCl3): δ 1.40 (t, J=7.0 Hz, 3H), 1.72-2.04 (m, 2H), 2.62-2.85 (m, 2H), 3.87 (s, 6H), 4.15 (q, J=7.0 Hz, 2H), 4.75 (d, J=10.5 Hz, 1H), 6.75-6.77 (dd, J=8.0 and 3.0 Hz, 1H), 7.01 (d, J=8.0 Hz, 2H), 7.12 (d, J=8.5 Hz, 1H), 7.29 (d, J=8.0 Hz, 2H), 7.44 (d, J=3.0 Hz, 1H). LRMS m/z 336.3 (calc for C21H24N2O2, M+, 336.2).

Workup

  1. customquenched with methanol
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washOrganic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel using 25% ethyl acetate-hexane as eluent

Sources & evidence

ORD record
ord-f757f9346cee4d12b22b241b46a0a908
Source dataset
uspto-grants-2012_12
Patent number
US08324262B2

Reaction notes

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