Cyclooctanol → HCID 53697156, compound

HRID 1154470Notes

Reaction equation

HRID 1154470 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:25]1(O)[CH2:32][CH2:31]CC[CH2:28][CH2:27][CH2:26]1>CCO.CCO.CCO.CCO.[Ti]>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH:19]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:32][CH2:31][CH2:20]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12766CyclooctanolHCID 53890667ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxylate

Product 1

HCID 53697156HCID 53697156, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 10.35 g (0.03 mmol) of ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1 carboxylate, 50 g of cyclooctanol and 2 g of tetraethyl orthotitanate is heated to 130° for 8 hours, a small amount of solvent being distilled off twice in vacuo. The mixture is subsequently evaporated in vacuo, the residue is taken up in chloroform and the solution is poured into about 20 percent hydrochloric acid. The mixture is stirred for 20 minutes, the chloroform phase is separated, washed successively with 1N hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated. By chromatography on a silica gel column while eluting with ethyl acetate and subsequent crystallization from ethyl acetate/hexane there is obtained cyclooctyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 183°-184°.

Workup

  1. temperatureis heated to 130° for 8 hours
  2. distillationa small amount of solvent being distilled off twice in vacuo
  3. customThe mixture is subsequently evaporated in vacuo
  4. additionthe solution is poured into about 20 percent hydrochloric acid
  5. customthe chloroform phase is separated
  6. washwashed successively with 1N hydrochloric acid and saturated sodium bicarbonate solution
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. washBy chromatography on a silica gel column while eluting with ethyl acetate and subsequent crystallization from ethyl acetate/hexane there

Sources & evidence

ORD record
ord-c9264760376f4cb69f4573df81c89b8d
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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