Potassium Hydroxide → Benzyl (3-{3-[bis(4-methoxybenzyl)amino]-4-chlorophenyl}oxetan-3-yl)acetate

HRID 1476062Notes

Reaction equation

HRID 1476062 reaction equation
[OH-].[K+].[O:3]1[CH2:6][C:5](=[CH:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4]1.[CH3:18][O:19][C:20]1[CH:46]=[CH:45][C:23]([CH2:24][N:25]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[C:26]2[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=2[Cl:32])=[CH:22][CH:21]=1>O1CCOCC1.C1=CCCC=CCC1.[Rh]Cl>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][N:25]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)[C:26]2[CH:27]=[C:28]([C:5]3([CH2:7][C:8]([O:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[O:9])[CH2:4][O:3][CH2:6]3)[CH:29]=[CH:30][C:31]=2[Cl:32])=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 54759148Benzyl (oxetan-3-ylidene)acetateHCID 58288209{3-[Bis(4-methoxybenzyl)amino]-4-chlorophenyl}boronic acid

Product 1

HCID 58288391Benzyl (3-{3-[bis(4-methoxybenzyl)amino]-4-chlorophenyl}oxetan-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 178420248HCID 178420248, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Under argon and at room temperature, 1.6 ml (2.37 mmol) of a 1.5 M aqueous potassium hydroxide solution, 272 mg (1.82 mmol) of benzyl oxetan-3-ylideneacetate and 750 mg (1.82 mmol) of {3-[bis(4-methoxybenzyl)amino]-4-chlorophenyl}boronic acid were added successively to a solution of 45 mg (0.09 mmol) of (1Z,5Z)-cycloocta-1,5-diene/rhodium(I) chloride dimer in 25 ml of dioxane. The reaction solution was then stirred at room temperature for 4 h. After the reaction had gone to completion, the solution was concentrated to dryness and the residue was taken up in 25 ml of water and 25 ml of ethyl acetate. The phases were separated and the aqueous phase was extracted three more times with ethyl acetate, and the combined organic phases were dried over magnesium sulphate and concentrated to dryness. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→1:1). This gave 669 mg (1.17 mmol, 64% of theory) of the title compound.

Workup

  1. concentrationthe solution was concentrated to dryness
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted three more times with ethyl acetate
  4. dry with materialthe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-df7395d4d20a4ff3bbc3aac5985796b8
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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