Tetrahydrofuran → (3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formate

HRID 458901Notes

Reaction equation

HRID 458901 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][C@@H:4]([O:7][C:8]([C:10]2([OH:23])[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:9])[CH2:3]1.ClC[CH2:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].[CH2:36]1COCC1>>[CH:8]([O-:9])=[O:7].[OH:23][C:10]1([C:8]([O:7][C@@H:4]2[CH2:5][CH2:6][N+:2]([CH3:36])([CH2:1][CH2:26][CH2:27][C:28](=[O:29])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:3]2)=[O:9])[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2535334-ChlorobutyrophenoneHCID 866022599-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester

Product 1

HCID 69480233(3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formateYield 7%

Procedure

0.575 g (1.858 mmol) of 9-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester (Intermediate I-10) and 1.018 g (5.576 mmol) of 4-chloro-1-phenylbutan-1-one in 6 ml of THF were refluxed for 20 days. After this time THF was poured off, and the residue was washed with THF in order to eliminate the alkylating agent. The product obtained (234 mg) was purified by preparative HPLC-MS to give 65 mg (7%) of the title compound (mixture of two stereoisomers) as a formate.

Workup

  1. washthe residue was washed with THF in order
  2. customThe product obtained (234 mg)
  3. customwas purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-ba177025df364778812fcbc2e80f418b
Source dataset
uspto-grants-2007_03
Patent number
US07192978B2

Reaction notes

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