Cyclopropanemethanol → HCID 53743479, compound

HRID 1154468Notes

Reaction equation

HRID 1154468 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]3[C@@H:9]3[CH2:20][CH2:21][CH2:22][N:8]3[C:7](=[O:23])[C:6]=2[CH:24]=1.O[CH2:26][CH:27]1CC1>CCO.CCO.CCO.CCO.[Ti]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH:19]4[CH2:27][CH2:26]4)=[O:16])=[C:10]3[C@@H:9]3[CH2:20][CH2:21][CH2:22][N:8]3[C:7](=[O:23])[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 10382951HCID 10382951, compound

Product 1

HCID 53743479HCID 53743479, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

6.92 g (20 mmol) of ethyl (S)-7-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 20 g of hydroxymethyl-cyclopropane and 1 g of tetraethyl orthotitanate are heated to 130° for 16 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 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 crystallization from ethyl acetate there is obtained cyclopropylmethyl (S)-7-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 146°-148°.

Workup

  1. customevaporated in vacuo
  2. additionthe solution is poured into about 20 percent hydrochloric acid
  3. customthe chloroform phase is separated
  4. washwashed successively with 1N hydrochloric acid and saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customBy crystallization from ethyl acetate

Sources & evidence

ORD record
ord-c03e85cf08ab42e09360b5c93cc6359c
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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