Pyridine → (2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile

HRID 1869645

반응식

HRID 1869645 반응식
[Br:1][CH2:2][C:3](Br)=[O:4].[NH:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]#[N:12].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][CH2:2][C:3]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]#[N:12])=[O:4]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 5706552(2S)-pyrrolidine-2-carbonitrile

생성물 1

HCID 11031276(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile수율 82.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회

실험 절차

To a cold solution (−10° C.) of bromoacetyl bromide (2.0 g, 10.0 mmol) in CH2Cl2 (30 mL), a solution of (S)-pyrrolidine-2-carbonitrile (480 mg, 5.0 mmol) and pyridine (1.4 g, 210 mmol) together with a catalytic amount of DMAP (50 mg) in CH2Cl2 (10 mL) was added over a 30 minute period. After stirring for about 10 minutes, the reaction temperature was gradually increased to room temperature. Stirring at room temperature was continued overnight. The residue was diluted with CH2Cl2 (60 mL), washed with ice water and cold 10% sodium bicarbonate aqueous solution to give crude product (1.01 g; yield of 93%). Column chromatography purification of the crude product resulted in pure 1-(2-bromo-acetyl)-(S)-pyrrolidine-2-carbonitrile (892 mg; 82.6% yield).

후처리

  1. stirringStirring at room temperature
  2. waitwas continued overnight
  3. washwashed with ice water and cold 10% sodium bicarbonate aqueous solution
  4. customto give crude product (1.01 g; yield of 93%)
  5. customColumn chromatography purification of the crude product

출처 및 근거

ORD 기록
ord-215d032144eb482e9e54cb7de404639e
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638638B2

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