Triethylamine → (3S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol

HRID 423400Notes

Reaction equation

HRID 423400 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[OH:9][C@H:10]1[CH2:14][CH2:13][NH:12][CH2:11]1.CCN(CC)CC>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]2[CH2:13][CH2:14][C@H:10]([OH:9])[CH2:11]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 34181101(3S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-olYield 72.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Heat 5-bromo-2-fluoro-pyridine (10.33 g, 57.39 mmmol) in THF (50 mL) with (S)-3-hydroxypyrrolidine (5.00 g, 57.39 mmol) and Et3N (9.2 mL, 68.87 mmol) in a microwave reactor at 120° C. for 45 min. Dilute with EtOAc (150 mL), and wash with saturated NaHCO3 (2×50 mL) and water (100 mL). Dry with Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 100% EtOAc to give 10.13 g (72%) of the title compound. MS/ES m/z (79Br) 244.0 [M+H]+.

Workup

  1. washwash with saturated NaHCO3 (2×50 mL) and water (100 mL)
  2. dry with materialDry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by chromatography
  6. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-51f72bc3e37d45a797df0ed851c6f8c2
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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