Ethyl Acrylate → Ethyl 3-{4-[2-ethyl-3-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-piperidinyl}propanoate

HRID 1942688Notes

Reaction equation

[CH2:1]([C:3]1[C:8]([B:9]2[O:13][C:12]([CH3:15])(C)[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:2].C1CCN2C(=NCCC2)CC1.[C:35]([O:39][CH2:40][CH3:41])(=[O:38])[CH:36]=[CH2:37]>C(#N)C>[CH2:1]([C:3]1[C:8]([B:9]2[O:10][C:11]([CH3:16])([CH3:17])[CH:12]([CH3:15])[O:13]2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH:18]1[CH2:23][CH2:22][N:21]([CH2:37][CH2:36][C:35]([O:39][CH2:40][CH3:41])=[O:38])[CH2:20][CH2:19]1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperidine (D119) (80 mg, 0.186 mmol) and DBU (0.034 mL, 0.224 mmol) in Acetonitrile (8 mL) was added ethyl 2-propenoate (57 mg, 0.499 mmol). The solution was sealed and stirred at 80° C. for 2 h. The solution was evaporated in vacuo to afford ethyl 3-{4-[2-ethyl-3-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-piperidinyl}propanoate (D123) (46 mg). MS (ES): C24H38BNO4 requires 415.3. found 416.3 (M+H+).

Workup

customThe solution was sealed
customThe solution was evaporated in vacuo

Sources & evidence

ORD record: ord-a3b25ae3d64145d4a8d53f6eedd7e03a
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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