Benzyl Bromide → HCID 67382789, compound

HRID 2176941Notes

Reaction equation

HRID 2176941 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH2:17]([NH:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10464431(1R,3S)-methyl 3-aminocyclopentanecarboxylate

Product 1

HCID 67382789HCID 67382789, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (462 mg, 3.30 mmol) was added to a solution of (1R,3S)-methyl 3-aminocyclopentanecarboxylate (400 mg, 2.22 mmol) in MeOH (10 ml) and stirred for 1 h. Benzyl bromide (0.2 ml, 1.8 mmol) was added to the reaction mixture and stirred for 15 h at 60-65° C. The reaction mixture was concentrated and the resulting residue was partitioned between water and CHCl3. The organic layer was separated and washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product. Purification by column chromatography over neutral alumina using 2% MeOH in CHCl3 as eluent afforded 180 mg of (1R,3S)-methyl 3-(benzylamino)cyclopentanecarboxylate with a purity of 75% which was proceeded for the next step.

Workup

  1. stirringstirred for 15 h at 60-65° C
  2. concentrationThe reaction mixture was concentrated
  3. customthe resulting residue was partitioned between water and CHCl3
  4. customThe organic layer was separated
  5. washwashed with water, brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford the crude product
  10. customPurification by column chromatography over neutral alumina using 2% MeOH in CHCl3 as eluent

Sources & evidence

ORD record
ord-dba732aad0b44eefb64f4ebb5625d7bc
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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