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

HRID 594384Notes

Reaction equation

HRID 594384 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-090ab0b42baf47889d987d836ecc4bdd
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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