Methanol → HCID 68773343, compound

(R)-tetrahydro-pyran-4-carboxylic acid (2-amino-2-phenyl-ethyl)-amide (450 mg, 1.82 mmol) was dissolved in dry THF; and 5.45 ml of borane-THF complex (1M in THF, 5.45 mmol) was added. The solution was refluxed for 3 hours. The reaction was then cooled to room temperature. Methanol (7 ml) was added slowly through the condenser, and the reaction brought to reflux for a further 15 minutes. The reaction was again cooled to room temperature; and the volatiles were removed under high vacuum. More methanol was added and subsequently evaporated (3×15 ml). The resulting residue was dissolved in ethylenediamine (7 ml) and the solution was heated to 60° C. for 20 minutes. The reaction was then quenched with the addition of a saturated aqueous solution of NaHCO3. This aqueous phase was extracted with DCM; and the organic extracts dried over Na2SO4. The solvent was removed in vacuo to give the crude product. Purification by flash chromatography over silica gel afforded (R)-1-Phenyl-N2-(tetrahydro-pyran-4-ylmethyl)-ethane-1,2-diamine (304 mg, 72%).

1. temperatureThe solution was refluxed for 3 hours
2. temperatureto reflux for a further 15 minutes
3. temperatureThe reaction was again cooled to room temperature
4. customand the volatiles were removed under high vacuum
5. additionMore methanol was added
6. customsubsequently evaporated (3×15 ml)
7. dissolutionThe resulting residue was dissolved in ethylenediamine (7 ml)
8. temperaturethe solution was heated to 60° C. for 20 minutes
9. customThe reaction was then quenched with the addition of a saturated aqueous solution of NaHCO3
10. extractionThis aqueous phase was extracted with DCM
11. dry with materialand the organic extracts dried over Na2SO4
12. customThe solvent was removed in vacuo
13. customto give the crude product
14. customPurification by flash chromatography over silica gel

ORD record

ord-a166b4ccc3a64d1fac7ed466c83da6e7

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790747B2