(1R,2R)-methyl 1-amino-2-(4-bromophenyl)cyclopropanecarboxylate hydrochloride → methyl (1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylate

HRID 600309ノート

反応式

HRID 600309 の反応式
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

参加物

5

反応物 2

HCID 67268087(1R,2R)-methyl 1-amino-2-(4-bromophenyl)cyclopropanecarboxylate hydrochlorideHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c783e0c48a64316b183852c484a6ab2
出典データセット
uspto-grants-2011_03
特許番号
US07902181B2

反応ノート

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