Azetidine → 1-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-methylphenyl]ethanone

HRID 1850716Notes

Reaction equation

HRID 1850716 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:20]1[CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:20]1([C:16](=[O:18])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[CH3:19])[CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 3907176[4-(Benzyloxy)-2-methylphenyl]acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 708190121-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-methylphenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[4-(benzyloxy)-2-methylphenyl]acetic acid (0.5 g, 1.951 mmol) was dissolved in DMF (1 ml) and azetidine (0.167 g, 2.93 mmol), DIEA (0.511 ml, 2.93 mmol), and HATU (1.484 g, 3.90 mmol) added. The mixture was stirred at RT for 1 hr. The reside was purified by column chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 10-100% water:acetonitrile+0.05% formic acid. to afford the title compound. LC/MS (m/z): 296 (M+H)+.

Workup

  1. customThe reside was purified by column chromatography

Sources & evidence

ORD record
ord-2f18708fd49d45a6b8d1805134b49318
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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