Aluminium lithium hydride → HCID 59332856, compound

HRID 340839Notes

Reaction equation

HRID 340839 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 59332849HCID 59332849, compound

Product 1

HCID 59332856HCID 59332856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LAH (2.5 mL, 2.52 mmol) was added a solution of (S)-7-bromo-3-methyl-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one (375 mg, 1.26 mmol) in THF (10 mL) at 0° C. 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), and extracted with ethyl acetate (4×15 mL), dried over sodium sulfate and concentrated. Preparative HPLC was used to purify the title compound as a white solid (166 mg, 55%): 1H NMR (400 MHz, CDCl3) δ8.10 (d, J=2.4 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 4.36 (2s, 2H), 4.21 (d, J=14.3 Hz, 1H), 6.33-3.61 (m, 2H), 3.26-3.13 (m, 1H), 1.36 (d, J=6.4 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. customto purify the title compound as a white solid (166 mg, 55%)

Sources & evidence

ORD record
ord-143d613031094486835b32c65c0a6ba8
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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