Diethyl Ether → 3-(2-Cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1-(methoxycarbonylmethyl)-1-methylpyrrolidinium bromide

HRID 469144ノート

反応式

HRID 469144 の反応式
[CH:1]1([C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[C:7]([O:9][CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:23][CH2:24][C:25]([O:27][CH3:28])=[O:26].C(OCC)C>C(#N)C.C(Cl)Cl>[Br-:23].[CH:1]1([C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[C:7]([O:9][CH:10]2[CH2:14][CH2:13][N+:12]([CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH3:15])[CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 25727N-Methyl-3-pyrrolidinyl CyclopentylmandelateHCID 60984Methyl bromoacetate

生成物 1

HCID 167228463-(2-Cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1-(methoxycarbonylmethyl)-1-methylpyrrolidinium bromide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

To compound 4 (0.8235 g, 2.71 mmol) in 30 ml of dry acetonitrile, methyl bromoacetate (1.08 g, 7.06 mmol) was added at room temperature. The mixture was stirred for 2 h. Evaporation of acetonitrile gave a crude product. The crude product was dissolved in a small volume of methylene chloride and then poured into 100 ml of dry ethyl ether to precipitate. This procedure was repeated three times to obtain Compound (a) as pure product (0.9912 g, 80%). White powder, m.p.: 192-194° C. Analysis for C21H30BrNOs. Calcd: C, 55.27; H, 6.63; N, 3.07. Found: C, 55.11; H, 6.59; N, 3.03. 1H NMR (CDCl3, 500 MHz): 1.23-1.29, 1.31-1.37, 1.41-1.47, 1.53-1.67 [8H, m, (CH2)], 2.18-2.23, 2.73-2.80, 4.04-4.16, 4.21-4.25 (6H, m, CH2NCH2CH2), 2.85 [1H, p, CHC(OH)], 3.57 (3H, s, NCH3), 3.80 (3H, s, CO2CH), 4.66, 4.85 (2H, 2dd, CH2CO2), 5.27 (1H, s, OH), 5.52 (1H, m, CO2CH), 7.25-728, 7.32-7.35, 7.57-7.59 (5H, m, Ph) ppm.

後処理

  1. customEvaporation of acetonitrile
  2. customgave a crude product
  3. customto precipitate

出典と根拠

ORDレコード
ord-5d01c7bc758f4a1f91b78c454e2a32b1
出典データセット
uspto-grants-2014_01
特許番号
US08628759B2

反応ノート

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