Cyclopentanone → Methyl1-[(cyclopentylamino)methyl]cyclopentane-1-carboxylate

HRID 2234511Notes

Reaction equation

HRID 2234511 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:10][NH2:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[C:12]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:10][NH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:4]

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 13285792Methyl 1-(aminomethyl)cyclopentanecarboxylate2×

Product 1

HCID 68683992Methyl1-[(cyclopentylamino)methyl]cyclopentane-1-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl1-(aminomethyl)cyclopentane-1-carboxylate (Intermediate 259; 1.5 g, 9.54 mmol) and cyclopentanone (1.0 mL, 11.45 mmol) were stirred in DCM (40 mL). Sodium acetate (940 mg, 11.45 mmol) and sodium triacetoxyborohydride (3.04 g, 14.31 mmol) were added. The mixture was stirred at room temperature for 48 hours. The reaction mixture was filtered and the filtrate concentrated. The residue was dissolved in methanol and absorbed on to an SCX column, which was then washed with methanol and eluted with ammonia in methanol. Product containing fractions were combined and evaporated to yield the title compound as a colourless oil (1.64 g, 81%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue was dissolved in methanol
  4. customabsorbed on to an SCX column, which
  5. washwas then washed with methanol
  6. washeluted with ammonia in methanol
  7. additionProduct containing fractions
  8. customevaporated

Sources & evidence

ORD record
ord-e9f0274a85684172b27426ecfdf37dd0
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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