Sodium Bicarbonate → HCID 57671202, compound

HRID 731340Notes

Reaction equation

HRID 731340 reaction equation
[CH3:1][N:2]([CH3:14])[N:3]=[C:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[CH3:1][N:2]([CH3:14])[NH:3][CH:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 69063730HCID 69063730, compound

Product 1

HCID 57671202HCID 57671202, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

The crude ethyl 2-(2,2-dimethylhydrazono)cyclopentanecarboxylate (6.91 mmol) was dissolved in acetic acid (10 mL) and water (10 mL). Sodium cyanoborohydride was added and the reaction was stirred at 25° C. for 16 h. The mixture was neutralized with saturated aqueous sodium bicarbonate solution until pH=8 was reached and was diluted with ethyl acetate (30 mL). After shaking, both layers were passed through a plug of Celite. The organic layer was further washed with saturated aqueous sodium bicarbonate solution (10 mL), saturated aqueous brine solution (10 mL), then dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product, ethyl 2-(2,2-dimethylhydrazinyl)cyclopentanecarboxylate as a clear oil, which was used directly in the next step without any further purification. LC-MS (ESI) calcd for C10H20N2O2 200.28, found 201.3 [M+H+].

Workup

  1. stirringAfter shaking
  2. washThe organic layer was further washed with saturated aqueous sodium bicarbonate solution (10 mL), saturated aqueous brine solution (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e24990c51e1e4a70906613b4c207ac4f
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

Loading…