Cyclopropanemethanol → HCID 53843677, compound

HRID 1154488Notes

Reaction equation

HRID 1154488 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12.O[CH2:25][CH:26]1CC1>CCO.CCO.CCO.CCO.[Ti]>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH:20]3[CH2:26][CH2:25]3)=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 10041121Ethyl (7S)-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate

Product 1

HCID 53843677HCID 53843677, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 6.22 g (20 mmol) of ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 1.52 g (6.7 mmol) of tetraethyl orthotitanate and 10 g (194 mmol) of hydroxymethyl-cyclopropane is stirred at 115° overnight, evaporated to dryness, the residue is taken up in methylene chloride and stirred for 0.5 hour with about 50 ml of water. The emulsion obtained is filtered through siliceous earth, the organic phase is washed with saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated. By recrystallization of the residue from ethyl acetate there is obtained cyclopropylmethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 189-190°.

Workup

  1. customevaporated to dryness
  2. stirringstirred for 0.5 hour with about 50 ml of water
  3. customThe emulsion obtained
  4. filtrationis filtered through siliceous earth
  5. washthe organic phase is washed with saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customBy recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-d7f1a027811d421382ec88c230e14a51
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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