Diisopropylethylamine → Methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoate

HRID 594384

反応式

HRID 594384 の反応式
[NH2:1][CH:2]([C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].CCN(C(C)C)C(C)C.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[C:31]([CH:39]=O)[CH:30]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH3:19][O:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:10]=1[CH:2]([NH:1][CH2:39][C:31]1[CH:30]=[N:29][C:38]2[C:33]([CH:32]=1)=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 836413-QuinolinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 69082713Methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate

生成物 1

HCID 69082480Methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoate

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of the chlorhydrate salt of methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate (1.177 g; 3.87 mmol; 1.0 equiv.) in anh. DCE (24 ml) was treated successively with DIPEA (1.35 ml; 7.75 mmol; 2.0 equiv.), quinoline-3-carbaldehyde (609 mg; 3.87 mmol; 1.0 equiv.), and NaBH(OAc)3 (1.150 g; 5.42 mmol; 1.4 equiv.). The resulting beige heterogeneous mixture was further stirred at rt, under nitrogen, for 2 h 45 min. DCM (50 ml) and a solution of aq. sat. NaHCO3 (35 ml) were then added. The organic layer was further washed with a solution of aq. sat. NaHCO3 (35 ml) and with brine (35 ml). The resulting yellow organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=10/1) afforded methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)-pentanoate as a yellow oil. LC-MS (conditions B): tR=0.66 min.; [M+H]+: 409.35 g/mol.

後処理

  1. washThe organic layer was further washed with a solution of aq. sat. NaHCO3 (35 ml) and with brine (35 ml)
  2. dry with materialThe resulting yellow organic layer was then dried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by FC (DCM/MeOH=10/1)

出典と根拠

ORDレコード
ord-090ab0b42baf47889d987d836ecc4bdd
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

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