1-Butanol → HCID 23000829, compound

HRID 397612Notes

Reaction equation

HRID 397612 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[C:6](/[CH:9]=[C:10]1\[CH2:11][N:12]([CH:17](C2CC2)[C:18]2[CH:19]([F:26])[C:20](=C=O)[CH:21]=[CH:22][CH:23]=2)[CH2:13][CH2:14][CH:15]\1[OH:16])([OH:8])=[O:7].Cl>C1C=CC=CC=1>[CH2:1]([O:8][C:6](/[CH:9]=[C:10]1\[CH2:11][N:12]([CH:17]([C:1]([CH:2]2[CH2:4][CH2:3]2)=[O:5])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:26])[CH2:13][CH2:14][CH:15]\1[OH:16])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 86759145HCID 86759145, compound

Product 1

HCID 23000829HCID 23000829, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

150 ml of 1-butanol were added to 3.19 g (9.58 mmol) of (E)-3-carboxymethylidene-1-(α-cyclopropyl-carbonyl-2-fluorobenzyl)-4-hydroxypiperidine. Hydrogen chloride gas was blown through the resulting mixture until the solution became acidic. After standing at room temperature for 2 hours, 100 ml of benzene were added and the mixture was subjected to azeotropic dehydration for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. Toluene and an aqueous solution of sodium bicarbonate were added to the residue. The toluene layer thus separated was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, followed by purification by chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=4/1), whereby 2.75 g (yield: 73.7%) of the tile compound were obtained as a pale yellow oil.

Workup

  1. waitthe mixture was subjected to azeotropic dehydration for 2 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionToluene and an aqueous solution of sodium bicarbonate were added to the residue
  5. customThe toluene layer thus separated
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customfollowed by purification by chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-e714d815589e4716af3a81dc6be951ea
Source dataset
uspto-grants-2003_08
Patent number
US06610708B1

Reaction notes

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