Imidazole → 3-(tert-Butyldimethylsilanyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 1014916노트

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HRID 1014916 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([OH:10])[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl.Cl>[CH3:1][O:2][C:3]([CH:5]1[CH:9]([O:10][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 147292541-(tert-Butyl) 2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

생성물 1

HCID 147292563-(tert-Butyldimethylsilanyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester수율 99%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A solution containing alcohol 38 (14.8 g, 60 mmol) in DCM (150 mL) was cooled to 0° C. To this solution was added imidazole (5.4 g, 79 mmol) followed by t-butyl-dimethylsilyl-chloride (10 g, 66 mmol) in two portions. The reaction mixture was warmed to ambient temperature over 1 h. After 5 h, the solution was diluted with 1M HCl and extracted twice with DCM. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 21.2 g (99%) of 39 as a yellow oil. 1H NMR (CDCl3, 300 MHz) δ4.38-4.34 (m, 1H), 4.18 (bs, rotomers, 0.5H), 4.04 (app d, J, =2.1 Hz, rotomers, 0.5H), 3.74 (s, 3H), 3.62-3.50 (m, 2H), 2.04-1.96 (m, 1H), 1.85-1.78 (m, 1H), 1.46 (s, minor rotomer), 1.41 (s, 9H), 0.92 (s, minor rotomer), 0.86 (s, 9H), 0.11 (s, 6H), 0.09 (s, minor rotomer) ppm.

후처리

  1. temperatureThe reaction mixture was warmed to ambient temperature over 1 h
  2. extractionextracted twice with DCM
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3c133a7ef3bc4036ad93d93e601dab17
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985735B2

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