Triethylamine → HCID 18766415, compound

HRID 480692Notes

Reaction equation

HRID 480692 reaction equation
[C:1]([O:5][C:6]([C:8]([CH3:22])([O:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][C:19](O)=[O:20])[CH:14]=[CH:15][CH:16]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[BH4-].[Na+]>O1CCCC1.O1CCCC1.O.O>[OH:20][CH2:19][CH2:18][CH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:8]([CH3:22])([CH3:9])[C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 18766458HCID 18766458, compound

Product 1

HCID 18766415HCID 18766415, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

3-[3-(1-tert-Butoxycarbonyl-1-methylethoxy)phenyl]propionic acid (10.0 g, 32.4 mmol) was dissolved in tetrahydrofuran (50 mL). Subsequently, triethylamine (3.6 g, 35.6 mmol) was added dropwise thereto. Ethyl chlorocarbonate (3.87 g, 35.6 mmol) was added under ice-cooling, and the mixture was stirred for one hour at room temperature. Sodium borohydride (2.45 g, 64.8 mmol) in tetrahydrofuran-water solution was added dropwise under ice-cooling, and the mixture was stirred for two hours at room temperature. Water was added thereto, and the reaction mixture was extracted with ethyl acetate. The organic layer was sequentially washed with diluted hydrochloric acid and saturated brine. The resultant mixture was subjected to drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=7/3), whereby the target compound was obtained (9.8 g (q.)).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for two hours at room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was sequentially washed with diluted hydrochloric acid and saturated brine
  6. dry with materialto drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=7/3), whereby the target compound
  7. customwas obtained (9.8 g (q.))

Sources & evidence

ORD record
ord-02c3b99c0ff542be8765b9e20bac5564
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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