Borane → HCID 86739321, compound

HRID 1903724Notes

Reaction equation

HRID 1903724 reaction equation
B.[Cl:2][N:3]1[CH2:9][C:8]2[CH2:10][CH:11]([C:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=O)[CH2:12][CH2:13][C:7]=2[N:6]2[C:22]3[CH:32]=[CH:31][N:30]=[CH:29][C:23]=3[C:24]3[C:25](=O)[CH2:26][CH:27]=[C:4]1[C:5]=32>O1CCCC1>[Cl:2][N:3]1[CH2:9][C:8]2[CH2:10][CH:11]([CH2:14][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:12][CH2:13][C:7]=2[N:6]2[C:22]3[CH:32]=[CH:31][N:30]=[CH:29][C:23]=3[C:24]3[CH2:25][CH2:26][CH:27]=[C:4]1[C:5]=32

Participants

4

Reactant 2

HCID 6331BoraneHCID 86739322HCID 86739322, compound

Product 1

HCID 86739321HCID 86739321, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in tetrahydrofuran (1 M, 50 ml) was added carefully to a stirred solution-suspension of 6-chloro-3-cyclohexylcarbonyl-1,2,3,4-tetrahydropyrido[4',3':2,3]indolo[1,7-ab][1,4]benzodiazepin-9(8H)-one (3.0 g) in tetrahydrofuran (100 ml) and the resulting mixture refluxed for 2 hours, cooled and the excess of borane destroyed by dropwise addition of water. The mixture was then evaporated to dryness under reduced pressure and the residue refluxed with a mixture of 1-octene (50 ml) and xylene (80 ml) for 1 hour and xylene and the combined filtrates were evaporated under reduced pressure. The residue was triturated with a small quantity of ether, filtered, and recrystallized from a mixture of 2-propanol and ethanol to yield the title compound, m.p. 230°-233° (dec.).

Workup

  1. temperaturethe resulting mixture refluxed for 2 hours
  2. temperaturecooled
  3. customthe excess of borane destroyed by dropwise addition of water
  4. customThe mixture was then evaporated to dryness under reduced pressure
  5. temperaturethe residue refluxed with a mixture of 1-octene (50 ml) and xylene (80 ml) for 1 hour
  6. customxylene and the combined filtrates were evaporated under reduced pressure
  7. customThe residue was triturated with a small quantity of ether
  8. filtrationfiltered
  9. customrecrystallized from a mixture of 2-propanol and ethanol

Sources & evidence

ORD record
ord-4c5af4b4878f4b6f94aa01cb67a17f76
Source dataset
uspto-grants-1984_03
Patent number
US04438120

Reaction notes

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