Sodium Carbonate → (R)-methyl 4-(1-(1-(3-fluorobenzyl)piperidine-2-carboxamido)cyclopropyl)benzoate

HRID 2273113Notes

Reaction equation

HRID 2273113 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br.C([O-])([O-])=O.[Na+].[Na+]>>[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([NH:9][C:10]1([C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)[CH2:12][CH2:11]1)=[O:8]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 680073-Fluorobenzyl bromideHCID 71204684HCID 71204684, compound

Product 1

HCID 71204706(R)-methyl 4-(1-(1-(3-fluorobenzyl)piperidine-2-carboxamido)cyclopropyl)benzoateYield 94.4%

Procedure

The title compound (D28) (62 mg) was prepared according to the general procedure for substituted benzyl amines preparation starting from (R)-methyl 4-(1-(piperidine-2-carboxamido)cyclopropyl)benzoate (D13) (50 mg, 0.16 mmol) and 3-fluoro benzyl bromide (0.03 ml, 0.25 mmol). (Na2CO3: 2.5 eq; reaction time: 6 hrs; 60° C.)

Sources & evidence

ORD record
ord-6d09fec9417545818655f64c17bfc262
Source dataset
uspto-grants-2015_09
Patent number
US09120824B2

Reaction notes

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