Acetic Acid → (R)-methyl 4-(1-(1-(4-fluoro-3-methylbenzyl)piperidine-2-carboxamido)cyclopropyl)benzoate

HRID 2273114Notes

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (R)-methyl 4-(1-(piperidine-2-carboxamido)cyclopropyl)benzoate (D13) (40 mg, 0.13 mmol) and 4-fluoro-3-methyl benzaldehyde (0.02 ml, 0.16 mmol), NaBH(OAc)3 (84 mg, 0.4 mmol) and CH3COOH (0.076 ml, 1.3 mmol) in DCM (10 ml) was heated at 110° C. (2 cycles of 5 min each) under microwave irradiation. The resulting mixture was purified by SPE-Si (2 g) eluting with a mixture DCM/AcOEt from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D29) (33 mg).

Workup

customunder microwave irradiation
customThe resulting mixture was purified by SPE-Si (2 g)
washeluting with a mixture DCM/AcOEt from 100/0 to 80/20
customCollected fractions after solvent evaporation

Sources & evidence

ORD record: ord-35cb982a00e44db0b4fc8a379edb7538
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120824B2

Reaction notes

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