2-Cyclopropylethan-1-ol → HCID 54557695, compound

HRID 1154496Notes

Reaction equation

HRID 1154496 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)[CH2:27][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[CH2:27][CH2:26]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1376422-Cyclopropylethan-1-olHCID 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 54557695HCID 54557695, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 3.45 g (10 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, 0.17 g (0.72 mmol) of tetraethyl orthotitanate and 7.5 g of 2-cyclopropyl-ethanol is stirred at 130° for 14.5 hours, about 2 ml of solvent being distilled off after 0.5 hour. The mixture is subsequently evaporated to dryness in vacuo, the residue is taken up in chloroform and chromatographed on silica gel while eluting with ethyl acetate. After crystallization of the resulting oil from ethyl acetate/n-hexane, there is obtained 2-cyclopropylethyl (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 163°-164°.

Workup

  1. distillationabout 2 ml of solvent being distilled off after 0.5 hour
  2. customThe mixture is subsequently evaporated to dryness in vacuo
  3. customchromatographed on silica gel
  4. washwhile eluting with ethyl acetate
  5. customAfter crystallization of the resulting oil from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-0013cd460ac44b738761fbd91ba72595
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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