Acetic Acid → rel-6-Bromo-N-[[(2R,6S)-tetrahydro-2,6-dimethyl-2H-pyran-4-yl]methyl]-2-pyridinamine
Reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH:6]([CH:8]=O)[CH2:5][C@H:4]([CH3:10])[O:3]1.[Br:11][C:12]1[N:17]=[C:16]([NH2:18])[CH:15]=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl.C(OCC)(=O)C>[Br:11][C:12]1[N:17]=[C:16]([NH:18][CH2:8][CH:6]2[CH2:7][C@H:2]([CH3:1])[O:3][C@H:4]([CH3:10])[CH2:5]2)[CH:15]=[CH:14][CH:13]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The mixture of (2R,6S)-2,6-dimethyltetrahydro-2H-pyran-4-carbaldehyde (120 mg, 0.84 mmol) and 6-bromo-2-aminopyridine (219 mg, 1.26 mmol) in 5 ml DCM was stirred at ambient temperature for about 40 min. To this solution was added sodium triacetoxy borohydride (268 mg, 1.26 mmol), followed by the addition of 0.01 ml acetic acid. The resulting solution was stirred at ambient temperature for about 40 hours. The reaction mixture was concentrated in vacuo to yield a residue was diluted with ethyl acetate, washed with sodium bicarbonate, brine, dried, concentrated. The resulting residue was purified by ISCO eluting with 10% to 20% ethyl acetate in heptane to yield 110 mg of the desired product as colorless oil. LCMS (m/z): 299/301 (MH+), retention time=1.01 min.
Workup
- stirringThe resulting solution was stirred at ambient temperature for about 40 hours
- concentrationThe reaction mixture was concentrated in vacuo
- customto yield a residue
- washwashed with sodium bicarbonate, brine
- customdried
- concentrationconcentrated
- customThe resulting residue was purified by ISCO
- washeluting with 10% to 20% ethyl acetate in heptane
Sources & evidence
- ORD record
- ord-21b5a36e635a49758fa172e03c1139c3
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778951B2
Reaction notes
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