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

HRID 1774932ノート

反応式

HRID 1774932 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8565fc24b86746b7b18fbe32d65dd710
出典データセット
uspto-grants-2016_02
特許番号
US09260434B2

反応ノート

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