1-Bromo-3-chloropropane → N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamide

HRID 403130ノート

反応式

HRID 403130 の反応式
[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])OC(C)(C)C)([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][CH2:26][CH2:27][Cl:28].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][N:9]([CH2:25][CH2:26][CH2:27][Cl:28])[CH2:10][CH2:11][NH:12][C:13](=[O:19])[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70896393Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate

生成物 1

HCID 67128436N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamide収率 55%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Compound 14 (1 g, 4.1 mmol), 1-bromo-3-chloropropane (9.7 g, 60 mmol) and K2CO3 (0.56 g, 4.09 mmol) were added to 50 mL CH3CN, and the solution was stirred for 48 h. The solvent was evaporated to dryness and the residue was purified on a silica gel TLC plate that was developed in 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2 yield the desired product as a pale yellow oil (55%). 1H NMR (CDCl3) δ 7.341 (d, 1H, Ar), 7.139 (dd, 1H, Ar), 7.029 (m, 1H, Ar), 6.995 (m, 1H, Ar), 3.592 (s, 2H, —CH2—), 3.539 (t, 2H, —CH2—), 3.167 (m, 2H, —CH2—), 2.583 (ddd, 2H, —CH2—), 2.519 (ddd, 2H, —CH2—), 1.900 (p, 2H, —CH2—), 1.425 (s, 9H, —C(CH3)3), 1.385 (s, 9H, —C(CH3)3). Mass Spec.=399.96 (M+H)+.

後処理

  1. customThe solvent was evaporated to dryness
  2. customthe residue was purified on a silica gel TLC plate that

出典と根拠

ORDレコード
ord-e0053acbb5fc43889d63d0b42d38387f
出典データセット
uspto-grants-2014_06
特許番号
US08747810B2

反応ノート

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