Triethylamine → HCID 15429325, compound

HRID 1831735Notes

Reaction equation

HRID 1831735 reaction equation
[CH2:1]1[CH:13]2[CH:4]([C:5](=[O:17])[NH:6][C:7]3[CH:8]=[C:9]([C:14](O)=[O:15])[CH:10]=[CH:11][C:12]=32)[CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C.CO>[OH:15][CH2:14][C:9]1[CH:10]=[CH:11][C:12]2[CH:13]3[CH2:1][CH2:2][CH2:3][CH:4]3[C:5](=[O:17])[NH:6][C:7]=2[CH:8]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 15429324HCID 15429324, compound

Product 1

HCID 15429325HCID 15429325, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 150 mg (0.65 mmol) of 1,2,3,3a,5,9b-hexahydrocyclopenta[c]-quinolin-4-one-7-carboxylic acid in 20 ml of THF is mixed with 0.10 ml (0.70 mmol) of triethylamine and 0.07 ml (0.70 mmol) of ethyl chloroformate at room temperature. After 10 minutes, 76 mg (2.0 mmol) of sodium borohydride is added, and within 20 minutes, 10 ml of methanol is added in drops to it. The batch is stirred for 15 hours at room temperature, diluted with ethyl acetate (100 ml), washed with 20% citric acid (50 ml) and saturated NaCl (50 ml), dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 65 mg of product.

Workup

  1. waitwithin 20 minutes
  2. washwashed with 20% citric acid (50 ml) and saturated NaCl (50 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-0a5682bbdfae4a239abf86538738a235
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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