Aluminium lithium hydride → HCID 59332833, compound

HRID 340840Notes

Reaction equation

HRID 340840 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:20]=[N:19][C:11]2[NH:12][C:13](=O)[C@@H:14]([CH3:17])[NH:15][CH2:16][C:10]=2[CH:9]=1>C1COCC1>[Br:7][C:8]1[CH:20]=[N:19][C:11]2[NH:12][CH2:13][C@@H:14]([CH3:17])[NH:15][CH2:16][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59332840HCID 59332840, compound

Product 1

HCID 59332833HCID 59332833, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° C.) of LAH (1M in THF, 4.4 mL, 4.4 mmol) was added a solution, of (R)-7-bromo-3-methyl-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one (750 mg, 2.9 mmol) in THF (20 mL). The reaction was warmed to room temperature and stirred over night. Once the reaction was complete, it was cooled to 0° C. and carefully quenched with water (10 mL), extracted with ethyl acetate (4×15 mL), dried over sodium sulfate and concentrated. The product was isolated by column chromatography (10% MeOH in CH2Cl2) to give the title compound as a light yellow solid (161 mg, 23%): 1H NMR (400 MHz, CD3OD) δ7.96 (s, 1H), 7.55 (s, 1H), 3.93-3.89 (d, J=15.6 Hz, 1H), 3.74-3.70 (d, J=15.2 Hz, 1H), 3.43-3.39 (d, J=13.6 Hz, 1H), 3.02 (m, 1H), 2.81-2.76 (m, 1H), 1.14-1.12 (d, J=6.8 Hz, 3H).

Workup

  1. temperatureit was cooled to 0° C.
  2. customcarefully quenched with water (10 mL)
  3. extractionextracted with ethyl acetate (4×15 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was isolated by column chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-880ec1a9f45341cc8fac750b1b9168dc
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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