tert-Butyl 3-bromopropionate → tert-Butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate

HRID 2404299

반응식

HRID 2404299 반응식
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].C(=O)(O)[O-].[Na+].Br[CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C(#N)C>[C:7]([C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][CH:9]=1)[CH2:3][N:2]([CH3:1])[CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])#[N:8]

참가 물질

5

반응물 3

HCID 256128tert-Butyl 3-bromopropionateHCID 4575953-(Methylaminomethyl)benzonitrileHCID 516892Sodium Bicarbonate

생성물 1

HCID 66678103tert-Butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred mixture of 3-[(methylamino)methyl]benzonitrile (6.1 g, 41.7 mmol) and sodium bicarbonate (7.0 g, 83.4 mmol) in ACN (70 mL) was added dropwise tert-butyl 3-bromo-propanoate (7 mL, 41.7 mol). After being stirred at RT for 12 hours, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.70 (s, 2H), 7.60 (m, 1H), 7.51 (m, 1H), 3.49 (s, 2H), 2.58 (m, 2H), 2.36 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

후처리

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by chromatography (silica, pet ether/EtOAc)

출처 및 근거

ORD 기록
ord-aac0c20924a245a68a4f003c4b3960e9
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802704B2

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