HCID 67268087, compound → methyl (1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylate

HRID 600309Notes

Reaction equation

HRID 600309 reaction equation
Cl.[NH2:2][C@:3]1([C:13]([O:15][CH3:16])=[O:14])[CH2:5][C@@H:4]1[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[H][H]>[Pd].CO>[NH2:2][C@:3]1([C:13]([O:15][CH3:16])=[O:14])[CH2:5][C@@H:4]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 67268087HCID 67268087, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14308470methyl (1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylateYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1R,2R)-methyl 1-amino-2-(4-bromophenyl)cyclopropanecarboxylate hydrochloride (120 mg) and palladium on carbon (10%) (47.3 mg) in methanol (20 mL) was stirred at 5 bar of hydrogen for 48 h. The catalyst was removed by filtration and the filtrate evaporated to dryness. The residue was purified by preparative HPLC on a Phenomenex Gemini column using a 95-5% gradient of aqueous 0.1% ammonia in acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford (1R,2R)-methyl 1-amino-2-phenylcyclopropanecarboxylate (18 mg) as a colourless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated to dryness
  3. customThe residue was purified by preparative HPLC on a Phenomenex Gemini column
  4. additionThe fractions containing the desired compound
  5. customwere evaporated to dryness

Sources & evidence

ORD record
ord-9c783e0c48a64316b183852c484a6ab2
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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