Triphenylphosphine → (RS)-N-(4-cyano-benzyl)-2-methoxy-2-[4-(1-methyl-piperidin-4-yloxy)-phenyl]-acetamide

HRID 1247261Notes

Reaction equation

[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][NH:8][C:9](=[O:20])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:43]1[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:20])[CH:10]([O:11][CH3:12])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:43]3[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]3)=[CH:15][CH:14]=2)=[CH:21][CH:22]=1)#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

(RS)-N-(4-Cyano-benzyl)-2-(4-hydroxy-phenyl)-2-methoxy-acetamide (example 21.2, 0.406 g) was dissolved in THF (12 ml). Triphenylphosphine (0.539 g) and 4-hydroxy-N-methylpiperidine (0.237 g) were added. The reaction mixture was cooled to 0° C. Slowly, DEAD (0.384 g) was added. The reaction mixture was stirred at 0° C. for 30 min and at rt for 5 days. The solvent was evaporated and the product was purified by chromatography (silicagel, mobile phase: gradient from CH2Cl2 to CH2Cl2/MeOH 4:1) to give (RS)-N-(4-cyano-benzyl)-2-methoxy-2-[4-(1-methyl-piperidin-4-yloxy)-phenyl]-acetamide as a colorless foam (0.241 g). MS 394.4 ([M+H]+)

Workup

customThe solvent was evaporated
customthe product was purified by chromatography (silicagel, mobile phase: gradient from CH2Cl2 to CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record: ord-ffb8b1f558da4d86b4e21c861461d2c7
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129238B2

Reaction notes

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