Diisopropylethylamine → (2S,3R)-Allyl 2-(((5-chlorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidine-1-carboxylate

HRID 60938Notes

Reaction equation

[NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11].Cl[C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:20]=2[N:21]=1.CCN(C(C)C)C(C)C>C(#N)C>[Cl:26][C:23]1[CH:24]=[CH:25][C:19]2[O:18][C:17]([NH:1][CH2:2][C@@H:3]3[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]3[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])=[N:21][C:20]=2[CH:22]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of (2S,3R)-allyl 2-(aminomethyl)-3-methylpiperidine-1-carboxylate (0.804 g, 3.787 mmol), 2,5-dichlorobenzo[d]oxazole (0.712 g, 3.787 mmol) and DIPEA (1 mL, 5.68 mmol) in acetonitrile (15 mL) was heated at 40° C. overnight. The solvent was removed in vacuo and the crude was purified via silica gel with 0˜100% EtOAc/hexanes to obtain the title compound. ESI-MS (m/z): 364 [M+1]+.

Workup

customThe solvent was removed in vacuo
customthe crude was purified via silica gel with 0˜100% EtOAc/hexanes

Sources & evidence

ORD record: ord-b5b1fb55534b4e929393c58e625fab2a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Reaction notes

Loading…