Methanol → (1R,9aR)-1-Methyloctahydro-2H-quinolizine

HRID 2175387Notes

Reaction equation

HRID 2175387 reaction equation
[C@H:1]1([CH2:11]N)[C@@H:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].CO>O>[CH3:11][C@H:1]1[C@H:10]2[CH2:9][CH2:8][CH2:7][CH2:6][N:5]2[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 6358779HCID 6358779, compound

Product 1

HCID 60028369(1R,9aR)-1-Methyloctahydro-2H-quinolizine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The lupinane amine.2HCl (1-[(1S,9aR)-octahydro-2H-quinolizin-1-yl]methanamine, CAS #: 75532-84-2, commercially available from ChemBridge, San Diego) (1.0 eq) was combined with 2,4-dichloro-5-X-pyrimidine (X=H, F, Cl, Me, CF3, CN, CONH2, OMe, NMe2) (1.0 eq) and NaHCO3 (1.2 eq). A mixture of MeOH:H2O (4/1) (concentration of the reaction mixture: ca. 0.1-0.5 M) was added and the resulting suspension was stirred for 1 d at RT. After the completion of the reaction was confirmed by TLC and HPLC, silica gel was added to the reaction mixture and solvents were evaporated under reduced pressure. The resulting solid was loaded on a CombiFlash column and further purified by flash chromatography eluting with DCM/MeOH—NH3 (2M) (gradient 0->10%).

Workup

  1. additionwas added to the reaction mixture and solvents
  2. customwere evaporated under reduced pressure
  3. customfurther purified by flash chromatography
  4. washeluting with DCM/MeOH—NH3 (2M) (gradient 0->10%)

Sources & evidence

ORD record
ord-c6e7ef7d835a4128a115247530da3b20
Source dataset
uspto-grants-2015_06
Patent number
US09062068B2

Reaction notes

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