Potassium Carbonate → cis-(2-Benzyloxyamino-cyclohexyl)-acetic acid ethyl ester

HRID 580878Notes

Reaction equation

HRID 580878 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[N:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2].[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[NH:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2].[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[NH:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 54396605(2-Benzyloxyimino-cyclohexyl)-acetic acid ethyl ester

Product 2

HCID 54235283cis-(2-Benzyloxyamino-cyclohexyl)-acetic acid ethyl esterYield 43%HCID 54235284trans-(2-Benzyloxyamino-cyclohexyl)-acetic acid ethyl esterYield 11%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(2-Benzyloxyimino-cyclohexyl)-acetic acid ethyl ester (4.66 g, 16.1 mmol) was taken up in 15 mL of acetic acid (AcOH) and NaBH3CN and stirred for 72 hours. Reaction was poured into NaHCO3 and extracted into EtOAc (3×30 mL). The combined organic layers were washed once with brine, dried over Na2SO4, filtered, and concentrated. The clear oil was dissolved in 50 mL of MeOH and K2CO3 (5.55 g, 40.2 mmol) was added and the reaction stirred for 12 hours. The reaction was concentrated, the residue taken up in CHCl3, filtered, and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) afforded 1.72 g (43%) of cis-(2-benzyloxyamino-cyclohexyl)-acetic acid ethyl ester and 0.441 g (11%) of trans-(2-benzyloxyamino-cyclohexyl)-acetic acid ethyl ester.

Workup

  1. customReaction
  2. extractionextracted into EtOAc (3×30 mL)
  3. washThe combined organic layers were washed once with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe clear oil was dissolved in 50 mL of MeOH
  8. concentrationThe reaction was concentrated
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by chromatography (SiO2, 4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-86065eba84324f649754c1e222f78a51
Source dataset
uspto-grants-1999_07
Patent number
US05919790

Reaction notes

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