3-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine → HCID 67586395, compound

HRID 1416633Notes

Reaction equation

HRID 1416633 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])[CH:5]=[N:6][CH:7]=1.[CH2:16]([Mg][Cl:21])[CH2:17][CH2:18][CH3:19]>CCOCC>[ClH:21].[ClH:21].[CH2:16]([C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])[CH:5]=[N:6][CH:7]=1)[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 112887213-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridineHCID 178418265HCID 178418265, compound

Product 1

HCID 67586395HCID 67586395, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a 1.08 g (4 mmol) sample of 5-bromo-3-((1-methyl-2-(S)-pyrrolidinyl)-methoxy)pyridine, prepared as in Example 56a above, dissolved in 40 mL of dry ether and cooled to 0° C. was added 6.0 mL of n-butylmagnesium chloride and 13.0 mg of Ni(dppp)Cl, and the reaction mixture was stirred for 5 hours at room temperature. The reaction was quenched by addition of satd NH4Cl, and the mixture was extracted with chloroform. The solvent was dried over MgSO4 and removed under vacuum, and the residue was purified of a column of silica gel, eluting with 100:1.25:0.025 chloroform:methanol:ammonium hydroxide. The product was converted into the title compound by treatment with HCl in ether according to Example 14c. MS (DCI/NH3) m/e: 259 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.28 (d, J=3.0 Hz, 1H), 8.24 (s, 1H), 7.80 (m, 1H), 4.58 (dd, J=11.0, 3.0 Hz, 1H), 4.42 (dd, J=11.4, 5.5 Hz, 1H), 3.96 (m, 1H), 3.77 (m, 1H), 3.32-3.23 (m, 1H), 3.05 (s, 3H), 2.78 (t, J=7.3, 2H), 2.43-2.38 (m, 1H), 2,26-2.06 (m, 3H), 1.70-1.60 (m, 2H), 1.40-1.27 (m, 2H), 0.91 (t, J=7.4 Hz, 3H). Anal. Calc. for C15H24N2O·2 HCl·0.2 ether: C, 56.46; H, 8.40; N, 8.33; Found C, 56.85; H, 8.73; N, 7.99. [α]25D =-7.30° (methanol).

Workup

  1. customThe reaction was quenched by addition of satd NH4Cl
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe solvent was dried over MgSO4
  4. customremoved under vacuum
  5. customthe residue was purified of a column of silica gel
  6. washeluting with 100:1.25:0.025 chloroform
  7. custom[α]25D =-7.30° (methanol)

Sources & evidence

ORD record
ord-3b8aaa979e8c4dfb8c870e5c6b5f02f0
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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