Sulfuric acid magnesium salt (1:1) → HCID 19384382, compound

HRID 2399749Notes

Reaction equation

HRID 2399749 reaction equation
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.S([O-])([O-])(=O)=O.[Mg+2].[C:17]([NH2:36])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>CO>[CH2:9]([O:8][C:6]([CH:4]1[CH2:5][CH:3]1[CH2:1][NH:36][C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 89334Ethyl 2-formylcyclopropanecarboxylate2×HCID 138598TritylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19384382HCID 19384382, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of ethyl 2-formylcyclopropane-1-carboxylate (1.00 g; 7.03 mmol) and magnesium sulfate (0.85 g; 7.03 mmol) in 50 ml methanol is added tritylamine (1.82 g; 7.03 mmol). To this is then added sodium cyanoborohydride (0.88 g; 14.06 mmol) and stirred for 48 hrs. To this is then further added 0.20 g of ethyl 2-formylcyclopropane-1-carboxylate and stirring continued for another 72 hrs. The reaction mixture is filtered, concentrated in vacuo and flash chromatographed using hexane:ethylacetate; 9:1 to obtain ethyl-2-triphenylmethylaminomethyl-cyclopropane-1-carboxylate as a colorless oil which is used directly in the next step.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated in vacuo and flash
  3. customchromatographed

Sources & evidence

ORD record
ord-60e278aaa5184f8e939b8e5c67939471
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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