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L-Prolinol → (S)-{1-[2-(4-Piperidin-4-yl-quinazolin-7-yloxy)-ethyl]-pyrrolidin-2-yl}-methanol

HRID 1170238
ノート
印刷プレビュー

反応式

HRID 1170238 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH2:25][CH2:26]OS(C)(=O)=O)=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[NH:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[CH2:37][OH:38]>CS(C)=O>[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH2:25][CH2:26][N:32]4[CH2:36][CH2:35][CH2:34][C@H:33]4[CH2:37][OH:38])=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 640091L-ProlinolHCID 595517384-[7-(2-Methanesulfonyloxy-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 12003708(S)-{1-[2-(4-Piperidin-4-yl-quinazolin-7-yloxy)-ethyl]-pyrrolidin-2-yl}-methanol

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

To a solution of 4-[7-(2-methanesulfonyloxy-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester (40.6 mg, 0.09 mmol) in DMSO (0.4 mL) was added (S)-(+)-2-pyrrolidinemethanol (90.9 mg, 0.9 mmol). The mixture was stirred at 120° C. overnight and subsequently partitioned between EtOAc and water. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was treated with 50% TFA/CH2Cl2 (8 mL) for 2 h, the solvents (TFA/CH2Cl2) were removed under reduced pressure to provide the desired product. LC-MS (ESI) calcd for C20H29N4O2 (MH+) 357.2, found 357.2.

後処理

  1. customsubsequently partitioned between EtOAc and water
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. additionThe residue was treated with 50% TFA/CH2Cl2 (8 mL) for 2 h
  6. customthe solvents (TFA/CH2Cl2) were removed under reduced pressure

出典と根拠

ORDレコード
ord-c6df735c52e94aad84aa455ae4c706d1
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07825244B2

反応ノート

読み込み中…

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