Triphenylphosphine → (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

HRID 1823025

反応式

HRID 1823025 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][O:30][C:31]([C@@H:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=2)[CH2:34]1)=[O:32].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:29][O:30][C:31]([C@@H:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42]([O:7][CH2:6][C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:41][CH:40]=2)[CH2:34]1)=[O:32]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 680224-Fluorobenzylic alcoholHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 785702(R)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

生成物 1

HCID 68614773(R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 550 mg (4.3 mmol) of 4-fluoro-benzylalcohol and 1.27 g (4.7 mmol) of triphenylphosphine in 7 ml of tetrahydrofurane is added dropwise at 0° C. to a solution of 1.11 g (4.7 mmol) of (R)-1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester and 1.01 g (4.7 mmol) of diisopropyl azodicarboxylate in 11 ml of tetrahydrofurane. The mixture is left to warm to RT and stirring is continued for 18 hours. For the working-up, after addition of 2 g of silica gel the reaction mixture is evaporated under reduced pressure. For purification, the material obtained is chromatographed on silica gel using first a 2:1-mixture, then a 1:1-mixture of heptane and ethyl acetate as the eluent. There are obtained 1.39 g (95% of theory) of (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a white solid; MS: m/e=344 (M+H)+.

後処理

  1. waitThe mixture is left
  2. additionafter addition of 2 g of silica gel the reaction mixture
  3. customis evaporated under reduced pressure
  4. customFor purification
  5. customthe material obtained
  6. customis chromatographed on silica gel using first a 2

出典と根拠

ORDレコード
ord-84b567fbb1984ea2ac48046d3b6551b1
出典データセット
uspto-grants-2006_05
特許番号
US07037935B2

関連ノート

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