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Triethylamine → (2S,4R)-1-Phenyl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697551
ノート
印刷プレビュー

反応式

HRID 1697551 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][NH:6]1)=[O:4].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:20])[F:21])(=[O:11])=[O:12])[CH2:7][N:6]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 66771131(2S,4R)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

生成物 1

HCID 66770633(2S,4R)-1-Phenyl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester収率 18.2%

試薬・触媒・溶媒 2

HCID 8895
Cupric acetate
触媒
HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S,4R)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (see example xx) (1.03 g, 1.0 eq) in dry dichloromethane (25 mL) were added freshly powdered molecular sieves (2.88 g). Phenyl boronic acid (0.74 g, 2.0 eq) was added, followed by triethylamine (0.62 g, 2.0 eq) and copper(II)acetate (0.61 g, 1.1 eq). Oxygen gas was bubbled through the reaction mixture for 5 min. The flask was sealed with a rubber septum and left under an atmosphere of oxygen by means of a balloon. After stirring at room temperature for 24 h, the mixture was filtered and the filtrate was treated with water and filtered again. The phases were separated and the organic phase dried over sodium sulfate, filtered and evaporated. Purification by flash chromatography on silica gel with an heptane/ethyl acetate gradient yielded the title compound as a light yellow solid (0.23 g, 18%). MS (ESI): m/z=414.2 [M+H]+.

後処理

  1. customOxygen gas was bubbled through the reaction mixture for 5 min
  2. customThe flask was sealed with a rubber septum
  3. waitleft under an atmosphere of oxygen by means of a balloon
  4. filtrationthe mixture was filtered
  5. additionthe filtrate was treated with water
  6. filtrationfiltered again
  7. customThe phases were separated
  8. dry with materialthe organic phase dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customPurification by flash chromatography on silica gel with an heptane/ethyl acetate gradient

出典と根拠

ORDレコード
ord-4447be48abcf402788d1d669a635423a
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163793B2

反応ノート

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