Triethylamine → HCID 67294374, compound

HRID 517947Notes

Reaction equation

HRID 517947 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][CH2:14][OH:15])[CH2:9]1.C(N(CC)CC)C.[Mn]([O-])(=O)(=O)=O.FC1C=CC=CN=1>CO>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][CH2:14][OH:15])[CH2:9]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97462-FluoropyridineHCID 24401PermanganateHCID 67294296HCID 67294296, compound

Product 1

HCID 67294374HCID 67294374, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

(S)-2-(Pyrrolidin-3-yl)ethanol 2-fluoropyridine (6.95 mmol, 0.598 ml, 0.674 g) and triethylamine (17.36 mmol, 2.420 ml, 1.757 g) were dissolved in MeOH (2.5 ml) and heated to 150° C. for 1 hour in the microwave. TLC (permanganate stain) suggested SM remained. Further 2-fluoropyridine (6.95 mmol, 0.598 ml, 0.674 g) was added and heating continued for 1 hour. The reaction mixture was concentrated in vacuo. The resulting residue was purified by silica chromatography, eluting with DCM—3% MeOH/DCM to afford (S)-2-(1-(pyridin-2-yl)pyrrolidin-3-yl)ethanol. 1H NMR (CDCl3) δ: 8.14 (d, 1H), 7.44 (m, 1H), 6.51 (m, 1H), 6.33 (d, 1H), 3.71 (m, 3H), 3.55 (m, 1H), 3.38 (m, 1H), 3.05 (m, 1H), 2.42 (m, 1H), 2.17 (m, 1H), 1.78 (m, 2H), 1.66 (m, 1H).

Workup

  1. temperatureheating
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe resulting residue was purified by silica chromatography
  4. washeluting with DCM—3% MeOH/DCM

Sources & evidence

ORD record
ord-541334860dac4c3f91a045b7ae3788d5
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

Loading…