Triethylamine → (S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methanol

HRID 517950

Reaction equation

HRID 517950 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([CH2:6][OH:7])[CH2:2]1.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C>CO>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:1]1[CH2:5][CH2:4][C@H:3]([CH2:6][OH:7])[CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97462-FluoropyridineHCID 7446911(3S)-3-Pyrrolidinemethanol

Product 1

HCID 67294196(S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methanolYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

(S)-Pyrrolidin-3-ylmethanol (9.89 mmol, 1 g), 2-fluoropyridine (29.7 mmol, 2.88 g) and triethylamine (49.4 mmol, 6.89 ml, 5.00 g) were dissolved in MeOH (2.5 ml) and heated to 150° C. for 1 hour in the microwave. The resulting residue was purified by silica chromatography, eluting with DCM—5% MeOH/DCM to afford (S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methanol (1.03 g).

Workup

  1. customThe resulting residue was purified by silica chromatography
  2. washeluting with DCM—5% MeOH/DCM

Sources & evidence

ORD record
ord-e80e2012ce1c4ce8aaec60440275cec8
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Linked notes

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