Sodium Chloride → methyl (1R,2R)-2-(hydroxymethyl)cyclopropane-1-carboxylate

HRID 456512Notes

Reaction equation

HRID 456512 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:7][C@H:6]1[C:8](O)=[O:9])=[O:4].B(OC)(OC)OC.[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:7][C@H:6]1[CH2:8][OH:9])=[O:4]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 8470Trimethyl borateHCID 12510972rac-(1R,2R)-2-(methoxycarbonyl)cyclopropane-1-carboxylic acid

Product 1

HCID 10931461methyl (1R,2R)-2-(hydroxymethyl)cyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-methyl sulfide complex (177 mL, 0.354 mol), slowly, by means of a dropping funnel, to a stirring solution of trans-cyclopropane-1,2-dicarboxylic acid monomethyl ester (Example 3a) (25.5 g, 0.177 mol), trimethyl borate (60.3 mL, 0.531 mol) and tetrahydrofuran (150 mL) at 0° C. After complete addition, allow the reaction to come to ambient temperature and stir for 2 h more. Pour the reaction mixture into a stirring solution of 50% aqueous sodium chloride solution (1.5 L)-concentrated HCl (10 mL). Extract the mixture with ethyl acetate (EtOAc) (3 times), combine the extracts, dry (Na2SO4) and concentrate the solvent to obtain a colorless oil: 22.6 g.

Workup

  1. additionAdd borane-methyl sulfide complex (177 mL, 0.354 mol)
  2. customat 0° C
  3. additionAfter complete addition
  4. customthe reaction
  5. customto come to ambient temperature
  6. extractionExtract the mixture with ethyl acetate (EtOAc) (3 times)
  7. dry with materialdry (Na2SO4)
  8. concentrationconcentrate the solvent
  9. customto obtain a colorless oil

Sources & evidence

ORD record
ord-d0f952f9aeea4e51aae9613756a290f2
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

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