Diethylamine → HCID 178464151, compound

HRID 1170434Notes

Reaction equation

HRID 1170434 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[CH2:14][C:13](=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>ClCCl>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([N:18]([CH2:19][CH3:20])[CH2:16][CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 15830669Benzyl 3-oxocyclobutane-1-carboxylate

Product 1

HCID 178464151HCID 178464151, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-oxocyclobutane carboxylic benzyl ester (88.1 mg, 0.43 mmol) in dichloromethane (4.3 mL) were successively added diethylamine (0.18 mL, 1.73 mmol) and sodium triacetoxyborohydride (137.0 mg, 0.65 mmol). The mixture was stirred at room temperature for 5 hours, and then to the reaction solution was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then evaporated. The resulting residue was purified by silica gel column chromatography (chloroform/methanol 20/1 to 5/1) to give the titled compound (66.3 mg, 59%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol 20/1 to 5/1)

Sources & evidence

ORD record
ord-73f160208dc54504a095dc7c7c5a528c
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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