Dibenzylamine → HCID 59204290, compound

HRID 2242210Notes

Reaction equation

HRID 2242210 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:30]([O:32][C:33]([CH:35]1[CH2:38][C:37](=O)[CH2:36]1)=[O:34])[CH3:31]>C(O)(=O)C.C1COCC1>[CH2:30]([O:32][C:33]([CH:35]1[CH2:38][CH:37]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:36]1)=[O:34])[CH3:31]

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22467070Ethyl 3-oxocyclobutanecarboxylate

Product 1

HCID 59204290HCID 59204290, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

Dibenzyl amine (0.150 g, 0.77 mmol) and sodium triacetoxyborohydride (0.300 g, 1.4 mmol) were added to a solution of 3-oxo-cyclobutanecarboxylic acid ethyl ester (0.100 g, 0.700 mmol) and acetic acid/THF (10%, 4.4 mL), stirred at room temperature for 72 hours and concentrated in vacuo. The resulting residue was dissolved in dichloromethane, washed with water, saturated NaHCO3 and brine, dried (Na2SO4) and concentrated in vacuo to give crude product. Purification by flash chromatography (silica, 1:9-3:7 EtOAc:hexanes) provided the title compound (0.180 g, 73% yield, 10:1 cis:trans ratio) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in dichloromethane
  3. washwashed with water, saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give crude product
  7. customPurification by flash chromatography (silica, 1:9-3:7 EtOAc:hexanes)

Sources & evidence

ORD record
ord-7e59cd6b8033409ca1a71d33a5274434
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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