Dimethylformamide → (9H-fluoren-9-yl)methyl 4-(chlorocarbonyl)piperidine-1-carboxylate

HRID 522860Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C=O)C.C(Cl)(=O)C([Cl:35])=O>C(Cl)Cl>[Cl:35][C:24]([CH:21]1[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:14][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[O:17])[CH2:19][CH2:20]1)=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of piperidine-1,4-dicarboxylic acid mono-(9H-fluoren-9-ylmethyl) ester (5 g, 14.2 mmol) in CH2Cl2 (50 mL) was added DMF (0.5 mL) and the resulting solution was cooled to 0° C. To this solution oxalyl chloride (3.6 g, 28.44 mmol) was added dropwise and the reaction mixture was stirred at RT for 16 h. The reaction mixture was concentrated under reduced pressure to afford (9H-fluoren-9-yl)methyl 4-(chlorocarbonyl)-piperidine-1-carboxylate (5 g, 95%) as brown liquid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-e9ac1ad3f9454cbc96488f1c7be1046b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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