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

HRID 219883

반응식

HRID 219883 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+].[C:17]([O:21][C:22](=[O:26])[CH2:23][CH2:24]Br)([CH3:20])([CH3:19])[CH3:18]>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])[CH2:24][CH2:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:26])#[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 solution of 3-[(methylamino)methyl]benzonitrile (6.1 g, 0.0417 mol) and sodium bicarbonate (7 g, 0.0834 mol) in acetonitrile (70 mL) under N2, was added tert-butyl-3-bromo-propanoate (7 mL, 0.0417 mol) in dropwise. After being stirred at RT for 12 h, the reaction mixture was filtered and the filterate was concentrated under reduced pressure. The obtained crude was purified using column chromatography on neutral silica gel (pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.69-7.70 (s, 2H), 7.59-7.61 (m, 1H), 7.49-7.53 (m, 1H), 3.49 (s, 2H), 2.56-2.59 (m, 2H), 2.34-2.38 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

후처리

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filterate was concentrated under reduced pressure
  3. customThe obtained crude
  4. customwas purified

출처 및 근거

ORD 기록
ord-557cfc614035461eb285200d40656b02
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

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