Methyl chloroformate → (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate

HRID 1619509ノート

反応式

HRID 1619509 の反応式
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].C(N(CC)CC)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[CH3:31][O:30][C:29]([NH:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]2)[CH2:9]1)=[O:6])=[O:32]

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

生成物 1

HCID 67607568(R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate収率 40.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (150 mg, 0.45 mmol) in DCM (5 ml), were added triethylamine (188 μl, 1.35 mmol) and methyl carbonochloridate (41.7 μl, 0.54 mmol). The reaction was stirred at RT for 4 hours, and then the solvent was evaporated. The residue was taken up with EtOAc and washed with water and brine. The organic phase was dried over Na2SO4 and evaporated to obtain (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate (58.0 mg; 40% yield). The compound was used in the next step without any further purification.

後処理

  1. customthe solvent was evaporated
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated

出典と根拠

ORDレコード
ord-b57e3d1877d346b2bc54c2fe27955ffa
出典データセット
uspto-grants-2014_07
特許番号
US08772314B2

反応ノート

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