Anthracene-9-carbonyl chloride → HCID 87953484, compound

HRID 489910Notes

Reaction equation

HRID 489910 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[CH2:7]1)=[O:5])[CH3:2].[CH:17]1[C:30]2[C:21](=[CH:22][C:23]3[C:28]([C:29]=2[C:31](Cl)=[O:32])=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:19][CH:18]=1>>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:16][CH2:15][N:14]([C:31]([C:29]3[C:30]4[C:21]([CH:22]=[C:23]5[C:28]=3[CH:27]=[CH:26][CH:25]=[CH:24]5)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:32])[CH2:13]2)[CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 167528Anthracene-9-carbonyl chloride2×HCID 69694575HCID 69694575, compound

Product 1

HCID 87953484HCID 87953484, compoundYield 100%

Procedure

The mixture of ethyl and isopropyl esters (1.23 g) was dissolved in anhydrous ethanol (˜50 mL) and dilute hydrochloric acid (2N, 4 mL) and 10% palladium on carbon (120 mg) was added. The suspension was shaken under hydrogen (48 psi) in a Parr shaker for 16 hr. Only a very small amount reduction occurred so the catalyst was filtered off and the solvent removed under vacuum. The residue was dissolved in glacial acetic acid, platinum (IV) oxide (100 mg) was added and the suspension shaken under 50 psi hydrogen at 60° C. overnight. The solvent was evaporated under vacuum, the residue dissolved in dichloromethane/methanol and the catalyst was filtered off though Celite®. The solvent was again evaporated and the residue partitioned between dilute hydrochloric acid and ethyl acetate (×3). The aqueous layer was made basic with 14% w/v sodium hydroxide and re-extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The product was purified by chromatography on silica gel eluting with 5%-10%-40%-methanol-dichloromethane to give (3R)-1-pyrrolidin-3-yl-piperidine-3-carboxylic acid ethyl ester (36.9 mg). This amine was reacted with anthracene-9-carbonyl chloride (Intermediate 3) by a procedure analogous to that described above for the preparation of Example 1 to give the title compound (70.1mg, 100%).

Workup

  1. customthat described above for the preparation of Example 1

Sources & evidence

ORD record
ord-ebd236b1035346718a014ef615bebcb8
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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