Acetic Acid → 1-Benzyl-2-methyl-azetidine-2-carboxylic acid ethyl ester

HRID 408578

반응식

HRID 408578 반응식
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][CH2:9]Cl)[CH3:6])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(O)(=O)C>C1COCC1>[CH2:1]([O:3][C:4]([C:5]1([CH3:6])[CH2:9][CH2:8][N:7]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:18])[CH3:2]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 3251421Potassium bis(trimethylsilyl)amideHCID 705577792-[Benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester

생성물 1

HCID 705586581-Benzyl-2-methyl-azetidine-2-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

A solution of 2-[benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester (1 eq.) in dry THF was cooled to −78° C. under nitrogen. KHMDS (15% w/w in toluene) (1.25 eq.) was slowly added so that temperature was kept below −65° C. The reaction was stirred for 1 h at −70° C. Then acetic acid (0.3 eq.) was added. The reaction was warmed to 20° C. and stirred for 10 min, then quenched with a saturated aqueous solution of NaHCO3 and partially concentrated under reduced pressure. The crude was extracted twice with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc 1/0 then 95/5) to afford 1-benzyl-2-methyl-azetidine-2-carboxylic acid ethyl ester.

후처리

  1. customwas kept below −65° C
  2. temperatureThe reaction was warmed to 20° C.
  3. stirringstirred for 10 min
  4. customquenched with a saturated aqueous solution of NaHCO3
  5. concentrationpartially concentrated under reduced pressure
  6. extractionThe crude was extracted twice with DCM
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude was purified by chromatography on silica gel (
  11. washelution with heptane/EtOAc 1/0

출처 및 근거

ORD 기록
ord-f490badee2424203bebb3fd33a4da7a0
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759334B2

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