Methanol → HCID 14156736, compound

HRID 579981Notes

Reaction equation

HRID 579981 reaction equation
[C:1]([CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[CH2:14][CH2:15][N:7]([C:8]=23)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4]1)#[N:2].[H-].C([Al+]CC(C)C)C(C)C.[H-].CO>ClCCl>[CH2:15]1[N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][C:9]=3[CH:3]([CH2:1][NH2:2])[NH:4][C:5]3[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=32)[CH2:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 166653HydrideHCID 14156732HCID 14156732, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14156736HCID 14156736, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Cyano-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (15 g) was added to 300 ml of a 1M solution of diisobutylaluminium hydride in dichloromethane at -78° C. The reaction mixture was stirred for 3 hours at low temperature and thereafter diluted to 1 liter with dichloromethane. The excess hydride was slowly decomposed with methanol (50 ml). The gelatinous solution was washed with 5% sodium hydroxide (500 ml) and brine (2×500 ml) and dried over anhydrous sodium sulfate. The solution was filtered and concentrated to a solid-oil mixture (15.2 g). Purification was effected by flash chromatography over silica gel (145 g, eluted with 3.5% methanol/dichloromethane) to afford 7.7 g of product. Recrystallization from hot ethanol (65 ml) yielded 6.2 g of crystals, m.p. 171.5°-172.5° C.

Workup

  1. washThe gelatinous solution was washed with 5% sodium hydroxide (500 ml) and brine (2×500 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered
  4. concentrationconcentrated to a solid-oil mixture (15.2 g)
  5. customPurification

Sources & evidence

ORD record
ord-25f10208a4f849a6a4ae97de2039a575
Source dataset
uspto-grants-1988_06
Patent number
US04751223

Reaction notes

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