Acetic Acid → HCID 23069873, compound

HRID 1436981Notes

Reaction equation

HRID 1436981 reaction equation
[N:1]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:18](O)(=O)[CH3:19].[C:22](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:23].[Na+].[OH-].[Na+]>O1CCCC1>[CH:18]1([CH2:19][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:2][CH2:3]2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 4384955Benzyl 1,4-diazepane-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23069873HCID 23069873, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 1-homopiperazinecarboxylate (1.95 g, 8.32 mmol) and cyclopropanecarboxyaldehyde (700 mg, 10.0 mmol) were dissolved in 40 mL of tetrahydrofuran. Acetic acid (600 mg, 10.0 mmol) and sodium triacetoxyborohydride (2.11 g, 10.0 mmol) were added thereto, and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was mixed with 1 N aqueous solution of sodium hydroxide, extracted with ethyl acetate twice, and the combined organic layers were washed with brine once. The mixture was dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (Fuji Silysia, NH Silica gel; ethyl acetate:hexane=50:50) to give benzyl 4-(cyclopropylmethyl)homopiperazin-1-carboxylate (2.5 g) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate twice
  2. washthe combined organic layers were washed with brine once
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (Fuji Silysia, NH Silica gel; ethyl acetate:hexane=50:50)

Sources & evidence

ORD record
ord-28457204853e4db0b70afadb5607f386
Source dataset
uspto-grants-2009_11
Patent number
US07619100B2

Reaction notes

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