Sodium Bicarbonate → (R/S) 6-(2-Carboxy-1-methyl-ethyl)-3,4-dihydro-2H-quinoline-1-carboxylic Acid 9H-Fluoren-9-ylmethyl Ester

HRID 396731Notes

Reaction equation

HRID 396731 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[CH:22]1[C:34]2[CH:33]([CH2:35][O:36][C:37](N3C(=O)CCC3=O)=[O:38])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1>CC(C)=O.O>[CH:22]1[C:34]2[CH:33]([CH2:35][O:36][C:37]([N:1]3[C:10]4[C:5](=[CH:6][C:7]([CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:9]=4)[CH2:4][CH2:3][CH2:2]3)=[O:38])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 108817731-Pyrrolidinecarboxylic acid, 2,5-dioxo-, 9H-fluoren-9-ylmethyl esterHCID 23003939(R/S) 3-(1,2,3,4-tetrahydro-quinolin-6-yl)-butyric acid

Product 1

HCID 54003742(R/S) 6-(2-Carboxy-1-methyl-ethyl)-3,4-dihydro-2H-quinoline-1-carboxylic Acid 9H-Fluoren-9-ylmethyl EsterYield 110.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of (R/S) 3-(1,2,3,4-tetrahydro-quinolin-6-yl)-butyric acid (2.6 g) and sodium bicarbonate (2.2 g) in acetone (40 ml) and water (40 ml) was treated with 2,5-dioxo-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (4.0 g) and the resulting mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate evaporated to low bulk. The residue was treated with dilute hydrochloric acid and the resulting gummy precipitate was extracted into a mixture of tetrahydrofuran, ethyl acetate and dichloromethane. This solution was washed with brine, then dried and then evaporated to give the title compound (5.8 g) as a light brown oil, which solidified on standing. MS (ES+) 464 (MNa+), MS (ES−) 440 (M−).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to low bulk
  3. additionThe residue was treated with dilute hydrochloric acid
  4. extractionthe resulting gummy precipitate was extracted into a mixture of tetrahydrofuran, ethyl acetate and dichloromethane
  5. washThis solution was washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d994ec8f12dd42d7a01bb8e7c35b26c4
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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