Ethyl 4-([1-(diphenylmethyl)azetidin-3-yl]oxy}-2-methyl-1-benzofuran-6-carboxylate → Ethyl 4-(azetidin-3-yloxy)-2-methyl-1-benzofuran-6-carboxylate

HRID 1643770Notes

Reaction equation

HRID 1643770 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([O:12][C:13]3[C:18]4[CH:19]=[C:20]([CH3:22])[O:21][C:17]=4[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=3)[CH2:9]2)C=CC=CC=1>CCOC(C)=O.CO.[Pd]>[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=2)[CH2:9]1

Participants

4

Reactant 1

HCID 59560418Ethyl 4-([1-(diphenylmethyl)azetidin-3-yl]oxy}-2-methyl-1-benzofuran-6-carboxylate

Product 1

HCID 59560268Ethyl 4-(azetidin-3-yloxy)-2-methyl-1-benzofuran-6-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of ethyl 4-{[1-(diphenylmethyl)azetidin-3-yl]oxy}-2-methyl-1-benzofuran-6-carboxylate (2.1 g, 4.77 mmol) in EtOAc/MeOH (10 mL/20 mL) and Pd/C (0.060 g, 10%, 0.048 mmol) was stirred for 14 hours under a hydrogen atmosphere (balloon). The mixture was filtered through a bed of Celite washing with methanol. The sample was concentrated to give a pale white solid (quantitative yield), which was used without further purification. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.35-1.52 (m, 3 H) 2.18 (s, 1 H) 2.47 (s, 3 H) 3.78-3.94 (m, 2 H) 4.00-4.13 (m, J=7.16 Hz, 2 H) 4.29-4.49 (m, 2 H) 5.11-5.27 (m, 1 H) 6.52 (s, 1 H) 7.05 (s, 1 H) 7.78 (s, 1 H); MS (ESI, pos): 276.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. washwashing with methanol
  3. concentrationThe sample was concentrated

Sources & evidence

ORD record
ord-a7c471976a564843833d8f5ee4c2f151
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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