Trimethylsilyldiazomethane → 9H-fluoren-9-ylmethyl-4-(diazoacetyl)piperidine-1-carboxylate

HRID 522861Notes

Reaction equation

HRID 522861 reaction equation
Cl[C:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:6][CH2:5]1)=[O:3].[Si]([CH:31]=[N+:32]=[N-:33])(C)(C)C>C1(C)C=CC=CC=1>[N+:32](=[CH:31][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:6][CH2:5]1)=[O:3])=[N-:33]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 86647451(9H-fluoren-9-yl)methyl 4-(chlorocarbonyl)piperidine-1-carboxylate

Product 1

HCID 866474499H-fluoren-9-ylmethyl-4-(diazoacetyl)piperidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of (9H-fluoren-9-yl)methyl 4-(chlorocarbonyl)piperidine-1-carboxylate (5 g, 13.6 mmol) in toluene at 0° C. was added TMS-diazomethane (30 mL). This reaction mixture was stirred at RT for 16 h. The reaction mixture was concentrated under reduced pressure to afford of (9H-fluoren-9-yl)methyl 4-(diazoacetyl)piperidine-1-carboxylate (5 g, 98%) as dark brown liquid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50c6eaa723f94a2e9b5db4a303a20b8d
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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