Ammonium Chloride → methyl 2-hydroxy-2-(1-methyl-1H-indol-3-yl)acetate

HRID 1288651ノート

反応式

HRID 1288651 の反応式
[Li+].CC([N-]C(C)C)C.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:11]1.CC1(C)[C@@]23[C@@]4(ON4S(=O)(=[O:32])C2)C[C@H]1CC3.[Cl-].[NH4+]>O1CCCC1>[OH:32][CH:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH3:9])[CH:11]=1)[C:20]([O:22][CH3:23])=[O:21]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 7128360(1S)-(+)-(10-Camphorsulfonyl)oxaziridineHCID 11106438Methyl 2-(1-methyl-1H-indol-3-yl)acetate

生成物 1

HCID 10932937methyl 2-hydroxy-2-(1-methyl-1H-indol-3-yl)acetate収率 66.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2.87 millimole of LDA in 5 mL of dry tetrahydrofuran at -78° C. was added dropwise a solution of 0.53 g of methyl 2-(1-methyl-3-indolyl)acetate in 5 mL of dry tetrahyrofruan. The mixture was stirred for 30 minutes at -78° C., and then 0.9 g of (+)-(2R,8aS)-(camphorsulfonyl)oxaziridine was added. The mixture was warmed to room temperature and stirred for 2 hours. Then the mixture was poured into a solution of saturated aqueous ammonium chloride, and then extracted with diethyl ether. The ether extract was dried with magnesium sulfate and concentrated by evaporation. The residue was subjected to silica gel chromatography using a developing solution of dichloromethane/ethyl acetate (98:2 by volume) to give 0.38 g of an oily product.

後処理

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 2 hours
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. dry with materialwas dried with magnesium sulfate
  6. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-bc29dd460ed14424aadf395cd905b66a
出典データセット
uspto-grants-1998_05
特許番号
US05747236

反応ノート

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