Isopropyl chloroformate → (3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Isopropyl Ester Hydrochloride

HRID 1182172ノート

反応式

HRID 1182172 の反応式
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][NH:21][CH2:20]4)[CH2:14][CH2:13]3)[C:9]2=[O:30])=[CH:5][CH:4]=1.[CH:33]([O:36][C:37]([Cl:39])=[O:38])([CH3:35])[CH3:34].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:39].[CH:33]([O:36][C:37]([N:21]1[CH2:22][C@H:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:19]([CH2:18][N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:30])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:32][CH:31]=4)[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)[CH2:20]1)=[O:38])([CH3:35])[CH3:34]

参加物

6

反応物 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 114646642-(4-Methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

生成物 1

HCID 67368814(3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Isopropyl Ester Hydrochloride収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(4-methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one (60 μmol) in anhydrous DCM (1 mL) was added isopropylchloroformate (180 μL, 1M in toluene, 180 μmol) and triethylamine (29 μL, 55 μmol). The reaction mixture was stirred overnight at room temperature. Saturated sodium bicarbonate aqueous solution was added to the reaction mixture and the aqueous layer washed with dichloromethane (3×2 mL). The organic layer was then concentrated in vacuo and purified by semi-preparative HPLC (Method D) and lyophilized to give the Compound 183 as a colorless solid (15.3 mg, 50%).

後処理

  1. washthe aqueous layer washed with dichloromethane (3×2 mL)
  2. concentrationThe organic layer was then concentrated in vacuo
  3. custompurified by semi-preparative HPLC (Method D)

出典と根拠

ORDレコード
ord-b70cd91e2a464b3f99dfe0e0782d4201
出典データセット
uspto-grants-2007_10
特許番号
US07288548B2

反応ノート

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