Cyclopentylamine → HCID 57635049, compound

HRID 2111255Notes

Reaction equation

HRID 2111255 reaction equation
[CH:1]1([NH:6][C:7]2[CH2:11][CH2:10][CH2:9][C:8]=2[C:12]([O:14][CH3:15])=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N)CCCC1.COC(C1CCCC1=O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(=O)C.[Na+]>ClCCl.C(#N)C.C(O)(=O)C>[CH:1]1([NH:6][CH:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[C:12]([O:14][CH3:15])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

9

Reactant 5

HCID 2906CyclopentylamineHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride2×HCID 131727418HCID 131727418, compound

Product 1

HCID 57635049HCID 57635049, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a ice cooled solution of 13.36 g (0.066 mole) of 2-cyclopentylamino-1-cyclopentenecarboxylic acid, methyl ester (prepared from 10.0 g (0.116 mole) of cyclopentylamine and 18.46 g (0.122 mole) of 2-oxocyclopentanecarboxylic acid methyl ester in 200 mL of dichloromethane, in the presence of 38.9 g (0.174 mole) of sodium triacetoxyborohydride and 14.31 g (0.174 mole) of sodium acetate) in 210 mL of acetonitrile and 110 mL of acetic acid was added 44.32 g (0.198 mole) of sodium triacetoxyborohydride. After 10 minutes, the cooling bath was removed and the mixture stirred at room temperature overnight. Solvents were removed under reduced pressure and the residue partitioned between ethyl acetate and water containing sufficient sodium carbonate to make the mixture basic (ca pH 11). The water layer was extracted twice with ethyl acetate and the combined ethyl acetate layers washed successively with water, then brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 10.2 g of (rac)-2-cyclopentylamino-cyclopentanecarboxylic acid, methyl ester, which was used without further purification in subsequent steps.

Workup

  1. customthe cooling bath was removed
  2. customSolvents were removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water containing sufficient sodium carbonate
  4. extractionThe water layer was extracted twice with ethyl acetate
  5. washthe combined ethyl acetate layers washed successively with water
  6. dry with materialbrine, dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f048bfbe4b0d49288462b2ab37d3462e
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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