1-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate → (S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl ester

HRID 1504325노트

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HRID 1504325 반응식
[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][C:8](=[O:11])[N:7]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:5].[CH3:19][Mg]Br>C1COCC1>[CH2:2]([O:3][C:4](=[O:5])[C@@H:6]([NH:7][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:9][C:8](=[O:11])[CH3:19])[CH3:1]

참가 물질

4

반응물 2

HCID 54611861-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylateHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 58544329(S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl ester수율 1,390.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-43 °C

실험 절차

A solution of (S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (20 g, 10 mmol) in dry THF (150 mL) was cooled to −50° C., and then methylmagnesium bromide (31 mL, 93.28 mmol) was added dropwise at a temperature between −50 and −44° C. in 30 min. The reaction mixture was stirred at −43° C. for 2 h and placed in a freezer (ca. −20° C.) overnight. The mixture was quenched with sat. NH4Cl solution and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (8:1-3:1 petroleum ether:EtOAc) to give the title intermediate (38 g) as light yellow oil. 1H NMR (400 MHz, CDCl3): δ(ppm) 5.11-5.09 (m, 1H), 4.25-4.24 (m, 1H), 4.19 (q, J=7.2 Hz, 2H), 2.63-2.52 (m, 2H), 2.15 (s, 3H), 2.12-2.08 (m, 1H), 1.92-1.82 (m, 1H), 1.44 (s, 9H), 1.28 (t, J=7.2 Hz, 3H).

후처리

  1. customplaced in a freezer (ca. −20° C.) overnight
  2. customThe mixture was quenched with sat. NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product, which
  8. customwas purified by column chromatography (8:1-3:1 petroleum ether:EtOAc)

출처 및 근거

ORD 기록
ord-9b127c8b82c6494b94f6b8c7a3049a10
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212168B2

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