2-Cyclohexylethanol → HCID 54172806, compound

HRID 1154471Notes

Reaction equation

HRID 1154471 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(CCO)[CH2:30][CH2:29][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][CH2:19][CH2:20][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 205082-CyclohexylethanolHCID 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 54172806HCID 54172806, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 6.93 g (0.02 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 1.4 g of tetraethyl orthotitanate and 24 g of 2-cyclohexyl-ethanol is heated to 140° for 2.5 hours, 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 15 minutes, the chloroform phase is separated, washed successively with 2N hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated. After chromatography on a silica gel column while eluting with ethyl acetate and subsequent crystallization from ethyl acetate/hexane, there is obtained 2-cyclohexylethyl (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 131°-132°.

Workup

  1. temperatureis heated to 140° for 2.5 hours
  2. customevaporated in vacuo
  3. additionthe solution is poured into about 20 percent hydrochloric acid
  4. customthe chloroform phase is separated
  5. washwashed successively with 2N hydrochloric acid and saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. washAfter chromatography on a silica gel column while eluting with ethyl acetate and subsequent crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c05527d9f3c7405d8d8e58498887b58d
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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