Tetrahydrofuran → (6-Aminopyridin-3-yl)methanol

HRID 861980Notes

Reaction equation

HRID 861980 reaction equation
P(C[C:6]1[N:11]2C=C(C(O)=O)[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)(O)(O)=O.[O:18]1CCC[CH2:19]1>>[NH2:14][C:10]1[N:11]=[CH:6][C:7]([CH2:19][OH:18])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 19701118HCID 19701118, compound

Product 1

HCID 2794829(6-Aminopyridin-3-yl)methanolYield 99%

Procedure

A 250 mL 3-neck flask equipped with an addition funnel, an argon (Ar) inlet and a stopper was flame dried and cooled to room temperature. Dry tetrahydrofuran (THF, 30 mL) was added to the flask, followed by 1M. lithium aluminum hydride (LAH) in Et2O (16 mL). After cooling the solution to 0° C. with a wet ice/water bath, the product from Example 8 (0.92 g, 6 mmol) suspended in THF (100 mL) was added dropwise. The reaction was allowed to warm to room temperature and stir for 3 h. The reaction was quenched with H2O, the salts filtered off and the filtrate stripped to give 0.591 g (99%) of title material.

Workup

  1. customA 250 mL 3-neck flask equipped with an addition funnel, an argon (Ar) inlet
  2. temperaturea stopper was flame
  3. customdried
  4. additionDry tetrahydrofuran (THF, 30 mL) was added to the flask
  5. temperatureAfter cooling the solution to 0° C. with a wet ice/water bath
  6. additionwas added dropwise
  7. temperatureto warm to room temperature
  8. customThe reaction was quenched with H2O
  9. filtrationthe salts filtered off

Sources & evidence

ORD record
ord-ca38f39571054032a43dce3d17c5611b
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

Loading…