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

HRID 219883

反応式

HRID 219883 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-557cfc614035461eb285200d40656b02
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

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