tert-Butyl acrylate → HCID 68814793, compound

HRID 2100674Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH:22]1[CH2:27][CH2:26][S:25][CH2:24][CH2:23]1)[O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[C:28]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])[CH:29]=[CH2:30].CCN(C(C)C)C(C)C>CO>[C:33]([O:32][C:28](=[O:31])[CH2:29][CH2:30][N:16]1[CH2:15][CH2:14][CH:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][O:5][C:4]3[CH:19]=[CH:20][C:21]([CH:22]4[CH2:27][CH2:26][S:25][CH2:24][CH2:23]4)=[C:2]([CH3:1])[CH:3]=3)=[CH:12][CH:11]=2)[CH2:18][CH2:17]1)([CH3:36])([CH3:35])[CH3:34]

Participants

Conditions

Temperature: 60 °C

Procedure

Crude 4-{4-[3-Methyl-4-(tetrahydro-thiopyran-4-yl)-phenoxymethyl]-phenyl}-piperidine is dissolved in MeOH (8 mL) and treated with t-butyl acrylate (1.777 mmol, 228 mg, 0.26 mL) and DIEA (4.442 mmol, 574 mg, 0.77 mL). The resulting mixture is heated at 60° C. for 45 minutes. After concentration, the residue is partially purified by silica gel chromatography (0 to 10% MeOH in DCM) to give crude 3-(4-{4-[3-Methyl-4-(tetrahydro-thiopyran-4-yl)-phenoxymethyl]-phenyl}-piperidin-1-yl)-propionic acid tert-butyl ester.

Workup

concentrationAfter concentration
customthe residue is partially purified by silica gel chromatography (0 to 10% MeOH in DCM)

Sources & evidence

ORD record: ord-08f704cd0b3d48918d383b140c22c27c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572811B2

Reaction notes

Loading…