Diethyl Ether → 1-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

HRID 1051839노트

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HRID 1051839 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15](Cl)Cl.C[Si](C=[N+]=[N-])(C)C.CCOCC>CO>[N:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:11]1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 27559811-Boc-Azetidine-3-carboxylic acid

생성물 1

HCID 446076271-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

1-(t-butoxycarbonyl)azetidine-3-carboxylic acid (2.03 g, 10.09 mmol) was dissolved in MeOH (10 ml) and DCM (10 mL) and then cooled to 0° C. A 2M solution of trimethylsilyldiazomethane in ether (7.57 ml, 15.1 mmol) was then added drop-wise over 5 minutes. The solution was stirred for 10 minutes at 0° C. and then warmed to room temperature over 30 minutes. The solution was concentrated under reduced pressure to remove volatiles to afford crude 119, which was used directly in the next step without further purification. 1H NMR: 1.44 (s, 9H), 3.35 (m, 1H), 3.75 (s, 3H), 4.10 (d, 4H, J=7.6 Hz).

후처리

  1. temperaturewarmed to room temperature over 30 minutes
  2. concentrationThe solution was concentrated under reduced pressure
  3. customto remove volatiles
  4. customto afford crude 119, which
  5. customwas used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-fbe41c2954254c2482a399b489997861
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388191B2

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