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

HRID 1288651노트

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HRID 1288651 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc29dd460ed14424aadf395cd905b66a
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05747236

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