HCID 14156740, compound → HCID 14156741, compound

HRID 579984Notes

Reaction equation

HRID 579984 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[N:18]2[C:19]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[CH:14]([CH2:24][NH:25][CH:26]=O)[NH:15][C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=32)[CH2:8]1>O1CCCC1>[CH3:26][NH:25][CH2:24][CH:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[CH2:8][CH2:7][N:18]([C:19]=23)[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[NH:15]1

Participants

4

Reactant 2

HCID 14156740HCID 14156740, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14156741HCID 14156741, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (5.6 g) was charged to a solution of N-[1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-ylmethyl]-formamide (10.3 g) in tetrahydrofuran (300 ml) at 0° C. under nitrogen in two portions (two hours apart). The mixture was stirred at room temperature overnight. The excess lithium aluminum hydride was destroyed carefully with water (6 ml) and sodium hydroxide (6 ml) at 0° C. The mixture was stirred with an additional 18 ml of water for 1 hour. The aluminium salts were filtered off. The tetrahydrofuran solution was concentrated to a foam. This material was dissolved in dichloromethane (200 ml) and washed with brine (200 ml). The solvent was removed and the crude product purified by flash chromatography over a silica gel column (100 g of silica, eluted with 2% methanol/dichloromethane) to afford 9.8 g of product. Recrystallization from hot ethanol (50 ml) yielded 6.18 g of crystals, m.p. 126°-127° C.

Workup

  1. customThe excess lithium aluminum hydride was destroyed carefully with water (6 ml) and sodium hydroxide (6 ml) at 0° C
  2. stirringThe mixture was stirred with an additional 18 ml of water for 1 hour
  3. filtrationThe aluminium salts were filtered off
  4. concentrationThe tetrahydrofuran solution was concentrated to a foam
  5. dissolutionThis material was dissolved in dichloromethane (200 ml)
  6. washwashed with brine (200 ml)
  7. customThe solvent was removed
  8. customthe crude product purified by flash chromatography over a silica gel column (100 g of silica, eluted with 2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-de7579434fdf466eaf61cd72ef619eec
Source dataset
uspto-grants-1988_06
Patent number
US04751223

Reaction notes

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