Potassium Carbonate → (2R,5S)-4-Benzyl-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475481ノート

反応式

HRID 1475481 の反応式
C([O-])([O-])=O.[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][C@H:18]([CH2:20]Cl)[N:17]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:16][C@H:15]1[CH3:29])=[O:13])([CH3:10])([CH3:9])[CH3:8].Cl.[CH3:31][C@@H:32]1[CH2:37][O:36][CH2:35][CH2:34][NH:33]1>C(#N)C>[C:7]([O:11][C:12]([N:14]1[CH2:19][C@H:18]([CH2:20][N:33]2[CH2:34][CH2:35][O:36][CH2:37][C@H:32]2[CH3:31])[N:17]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:16][C@H:15]1[CH3:29])=[O:13])([CH3:10])([CH3:9])[CH3:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 57356922(3R)-3-Methylmorpholine hydrochlorideHCID 86724019tert-butyl (2R,5R)-4-benzyl-5-(chloromethyl)-2-methylpiperazine-1-carboxylate

生成物 1

HCID 86724030(2R,5S)-4-Benzyl-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester収率 69.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

K2CO3 (81.6 g, 591 mmol) and KI (73.6 g, 443 mmol) were added to a solution of (2R,5R)-4-benzyl-5-chloromethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (50 g, 147.9 mmol) in acetonitrile (400 mL) followed by (R)-3-methyl-morpholine hydrochloride (26.4 g, 192 mmol). The reaction was stirred at 70° C. for 18 h. The solid was then removed by filtration and the solvent removed in vacuo. The crude material was purified by chromatography using a pad of silica (20% EtOAc in Petrol) to give the title compound (41.3 g) as a white solid. MS: [M+H]+=404.

後処理

  1. customThe solid was then removed by filtration
  2. customthe solvent removed in vacuo
  3. customThe crude material was purified by chromatography

出典と根拠

ORDレコード
ord-4fe1cb013e1a47f0883e8eceadaaef93
出典データセット
uspto-grants-2015_04
特許番号
US09018214B2

反応ノート

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