Ethanolamine → HCID 19600009, compound

HRID 611245Notes

Reaction equation

HRID 611245 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH2:19][CH2:18][C:17]3[CH:20]=[C:21]([C:23]([OH:25])=O)[O:22][C:16]=3[CH2:15]2)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:26][CH2:27][CH2:28]O.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.O>[O:25]1[CH2:28][CH2:27][N:26]=[C:23]1[C:21]1[O:22][C:16]2[CH2:15][N:14]([C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:19][CH2:18][C:17]=2[CH:20]=1

Participants

8

Reactant 5

HCID 700EthanolamineHCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 19599954HCID 19599954, compound

Product 1

HCID 19600009HCID 19600009, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.884 g (2.590 mmol) of 6-(6-phenylhexanoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylic acid, 0.16 g (2.59 mmol) of 2-aminoethanol, 1.08 ml (7.77 mmol) of triethylamine and 2.50 ml (25.9 mmol) of carbon tetrachloride in 50 ml of acetonitrile, 2.04 g (7.77 mmol) of triphenylphosphine was added under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel flush column chromatography (ethyl acetate to ethyl acetate/methanol=20/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel
  6. customflush column chromatography (ethyl acetate to ethyl acetate/methanol=20/1)

Sources & evidence

ORD record
ord-daa68a339bbb495d8a1f11eb25a0cf09
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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