Hydrochloric Acid → HCID 69830962, compound

HRID 2305204Notes

Reaction equation

HRID 2305204 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:20]=1)(OC(C)(C)C)=O.[ClH:26]>C(Cl)Cl.CCOCC>[ClH:26].[ClH:26].[CH3:25][O:24][CH2:23][CH2:22][O:21][C:19]1[CH:20]=[C:15]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[CH:16]=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22961834HCID 22961834, compound

Product 1

HCID 69830962HCID 69830962, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-methoxyethoxypyridine from step 197e (480 mg, 1.36 mmol) in CH2Cl2 at 0° C. was added a solution of HCl in Et2O, and the solution was stirred for 2 h. The solvent was removed and the residue was recrystallized from EtOH/Et2O to afford the title compound (215 mg): mp 182-184° C.; [α]25D +22.8 (c 0.56, MeOH); 1H NMR (D2O, 300 MHz) δ 1.98 (m, 1H), 2.00-2.06 (m, 2H), 2.25 (m, 1H), 3.00 (m, 1H), 3.05 (s, 3H), 3.65 (t, 2H, J=6.0 Hz), 3.85 (t, 2H, J=6.0 Hz), 4.15 (m, 1H), 4.30-4.35 (m, 2H), 4.52 (m, 1H), 7.15 (t, 1H, J=3.0 Hz), 8.02 (br s, 2H); MS (CI/NH3) m/z 253 (M+H)+, 279 (M+NH4)+; Anal. Calcd for C13H20N2O3.2.1 HCl: C, 47.48; H, 6.77; N, 8.52. Found: C, 47.56; H. 6.83; N, 8.51.

Workup

  1. customThe solvent was removed
  2. customthe residue was recrystallized from EtOH/Et2O

Sources & evidence

ORD record
ord-fed0085f580144969f9893c054dfcaa6
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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