Sodium borohydride → HCID 59738310, compound

HRID 559517Notes

Reaction equation

HRID 559517 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([C:8]1([C:11](OC)=[O:12])[CH2:10][CH2:9]1)=[O:7].[BH4-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([C:8]1([CH2:11][OH:12])[CH2:9][CH2:10]1)=[O:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59738291HCID 59738291, compound

Product 1

HCID 59738310HCID 59738310, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(2-chlorobenzylcarbamoyl)cyclopropanecarboxylate (330 mg, 1.2 mmol) in THF (5 mL) and CH3OH (5 mL) was added sodium borohydride (93 mg, 2.4 mmol, 2 equiv.). The reaction mixture was stirred for 3 h and quenched with diluted AcOH. The reaction mixture was concentrated and dissolved in EtOAc. The organic layer was washed with saturated NaHCO3, H2O and brine, dried over Na2SO4, and concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give N-(2-chlorobenzyl)-1-(hydroxymethyl)cyclopropanecarboxamide (164 mg, 55%). LRMS (M+H+) m/z 240.0.

Workup

  1. customquenched with diluted AcOH
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in EtOAc
  4. washThe organic layer was washed with saturated NaHCO3, H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified on RP-HPLC
  8. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-da651eb0b05f423faea8ed5102ad82d3
Source dataset
uspto-grants-2011_11
Patent number
US08063082B2

Reaction notes

Loading…