Water → (S)-tert-butyl 3-(2-(2-hydroxyphenyl)quinolin-4-ylamino)pyrrolidine-1-carboxylate

HRID 2189204Notes

Reaction equation

HRID 2189204 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[CH:16]=1.O>CS(C)=O>[OH:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:17]1[CH:16]=[C:15]([NH:13][C@H:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 1355470522-(4-Chloroquinolin-2-yl)phenol

Product 1

HCID 136068479(S)-tert-butyl 3-(2-(2-hydroxyphenyl)quinolin-4-ylamino)pyrrolidine-1-carboxylateYield 42.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (S)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (0.218 g, 1.173 mmol) and 2-(4-chloroquinolin-2-yl)phenol (0.100 g, 0.391 mmol) in DMSO (2 mL) was heated under microwave conditions at 155° C. for 1.5 hours. The mixture was added to water (50 mL) and extracted with diethyl ether (2×20 mL). The organic layers were combined, dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (30-40% ethyl acetate/hexane) to give the title compound (0.067 g, 42%).

Workup

  1. extractionextracted with diethyl ether (2×20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography (30-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1f3f72d14b0242ebbd07d0804180dc75
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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