Methyl iodide → (2R,4R)-4-Methoxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

HRID 2217457노트

반응식

HRID 2217457 반응식
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].CI.[H-].[Na+].[CH3:34]COC(C)=O>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:34])[CH2:7][N:6]1[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:4]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 68685802(2R,4R)-4-Hydroxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

생성물 1

HCID 68806999(2R,4R)-4-Methoxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Into a solution of 2 (5.71 g, 14.7 mmol) in anhydrous DMF (20 mL) and anhydrous THF (20 mL) was added MeI (3.67 mL, 58.9 mmol). The solution was cooled to 0° C. in an ice bath and NaH (0.766 g, 19.2 mmol) was added in one portion. The mixture was stirred at RT for 26 h before adding EtOAc and washing sequentially with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. Purification of the crude material by flash chromatography revealed 3 (4.67 g, 79%) as a white solid.

후처리

  1. washwashing sequentially with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the crude material by flash chromatography

출처 및 근거

ORD 기록
ord-fd7139d14ae64c2180b70720f1a27396
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407972B2

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