Triethylamine → HCID 21700356, compound

HRID 1597443Notes

Reaction equation

HRID 1597443 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH:11][C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1.C(N(CC)CC)C>C1COCC1>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:14]1[CH2:15][CH2:16][CH:12]([OH:11])[CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 21700356HCID 21700356, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5.1 mL (44.6 mmol) of 2-chlorobenzoxazole in 35 mL of THF at 0° C. was added 4.28 g (49.0 mmol, 1.1 equiv.) of (R)-3-hydroxypyrrolidine and 4.42 mL (32 mmol, 0.72 equiv.) of triethylamine. The resulting solution was stirred 12 h at RT, the precipitate was filtered, washed with THF (3×5 mL), and the filtrate concentrated in vacuo. Purification by silica gel flash column chromatography using hexane/EtOAc 1/1 to EtOAc as eluent afforded 3.74 g of the title compound: low resolution MS (ESP) m/e 205 (MH+).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with THF (3×5 mL)
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-80986e6b086a453e992794a01c89b5da
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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