Triethylamine → HCID 57671194, compound

HRID 731336Notes

Reaction equation

HRID 731336 reaction equation
Cl.[CH2:2]([O:4][C:5]([C@H:7]1[C@@H:12]([NH2:13])[CH2:11][CH:10]=[CH:9][CH2:8]1)=[O:6])[CH3:3].C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2].[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[CH2:2]([O:4][C:5]([CH:7]1[CH:12]([NH:13][CH2:32][C:31]2[CH:34]=[CH:35][C:28]([F:27])=[CH:29][CH:30]=2)[CH2:11][CH:10]=[CH:9][CH2:8]1)=[O:6])[CH3:3]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 680234-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 17039344HCID 17039344, compound

Product 1

HCID 57671194HCID 57671194, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

cis-6-Amino-cyclohex-3-enecarboxylic acid ethyl ester hydrochloride (411.4 mg, 2 mmol) and anhydrous tetrahydrofuran (20 mL) were mixed to form slurry. Triethylamine (295 μL, 2.1 mmol), magnesium sulfate (685 mg), and 4-fluoro-benzaldehyde (450 μL, 4.1 mmol) were added at 25° C. and the resulted mixture was stirred at 25° C. for 16 h. The precipitated solid was filtered off and the filtrate was concentrated in vacuo at 25° C. to give an oil. This oil was dissolved in methanol (35 mL) and sodium borohydride (155 mg, 4.1 mmol) was then added portionwise at 25° C. The mixture was stirred at 25° C. for 1 h. Saturated aqueous sodium bicarbonate solution (15 mL) was added, extracted with ethyl acetate (3×40 mL) and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the desired product, 6-(4-fluoro-benzylamino)-cyclohex-3-enecarboxylic acid ethyl ester (537.6 mg, 1.94 mmol, 96.9%). This crude product was directly used in next step without further purification. LC-MS (ESI) calcd for C16H20FNO2 277.2, found 278.2 [M+H+].

Workup

  1. customto form slurry
  2. filtrationThe precipitated solid was filtered off
  3. concentrationthe filtrate was concentrated in vacuo at 25° C.
  4. customto give an oil
  5. stirringThe mixture was stirred at 25° C. for 1 h
  6. extractionextracted with ethyl acetate (3×40 mL)
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-432066c112804ec498ac4eef29a86c43
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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