Sodium Bicarbonate → HCID 57671233, compound

HRID 731298Notes

Reaction equation

HRID 731298 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH3:10])=[O:8].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[CH3:20].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C.C(O)(=O)C>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:1][C@H:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[C:7]([O:9][CH3:10])=[O:8])=[CH:14][C:13]=1[CH3:20]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 27348744-Fluoro-3-methylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 14698811methyl (1R,2S)-2-aminocyclopentane-1-carboxylate

Product 1

HCID 57671233HCID 57671233, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl (1R,2S)-2-aminocyclopentanecarboxylate (310 mg, 2.17 mmol) in methanol (10 mL) under a nitrogen atmosphere, 4-fluoro-3-methyl-benzaldehyde (0.27 mL, 2.17 mmol) was added. The mixture was stirred for 10 min, and then acetic acid (0.4 mL) was added followed by sodium cyanoborohydride (340 mg, 5.42 mmol). The resulting mixture was stirred at 25° C. for 16 h, and then poured into a mixture of saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (100 mL). Two layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous brine solution, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to afford the desired product, methyl (1R,2S)-2-[(4-fluoro-3-methylbenzyl)amino]cyclopentanecarboxylate (460 mg, 1.73 mmol, 80%), as a clear oil. 1H NMR (400 MHz, CDCl3) δ: 1.68 (2H, m), 1.89 (3H, m), 2.04 (1H, m), 2.28 (3H, d, J=2.0 Hz), 2.97 (1H, m), 3.31 (1H, m), 3.71 (3H, s), 3.72 (2H, m), 6.93 (1H, t, J=8.4 Hz), 7.07 (1H, m), 7.11 (1H, m).

Workup

  1. stirringThe resulting mixture was stirred at 25° C. for 16 h
  2. customTwo layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous brine solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-66763e1192ab4e7a9e38b2a50fe87060
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

Loading…