Carbon Dioxide → HCID 58066376, compound

HRID 2410501Notes

Reaction equation

HRID 2410501 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH3:13])=[C:4]([CH2:14][O:15][CH3:16])[CH:3]=1.C([Li])CCC.[C:22](=[O:24])=[O:23]>C1COCC1>[CH3:16][O:15][CH2:14][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH3:13])[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 280Carbon Dioxide2×HCID 58554132HCID 58554132, compoundHCID 178418339Butyllithium

Product 1

HCID 58066376HCID 58066376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[4-Bromo-2-(methoxymethyl)phenyl]-2-methylpyrrolidine (16.5 g, 58 mmol) in anhydrous THF (160 mL) was added n-butyl lithium in drops at −78° C. After 3 hours at −78° C., the reaction mixture was poured onto crushed dry-ice (100 g). Once the excess carbon dioxide was escaped, the reaction mixture was evaporated, and then acidified with 1.5 N HCl. The precipitate was filtered off and washed with pet ether to afford title compound as a solid. LC/MS (Method B): 249.9 (M+H)+. 1H NMR (DMSO-d6, 400 MHz) δ 12.4 (1H, brs), 7.84 (1H, s), 7.70 (1H, d), 6.85 (1H, d), 4.32-4.42 (2H, m), 3.59-3.87 (1H, m), 3.56 (1H, m), 3.29 (3H, s), 3.13 (1H, m), 2.14 (1H, m), 1.89 (1H, m), 1.74 (1H, m), 1.55 (1H, m), 0.99 (3H, d).

Workup

  1. additionthe reaction mixture was poured
  2. customthe reaction mixture was evaporated
  3. filtrationThe precipitate was filtered off
  4. washwashed with pet ether

Sources & evidence

ORD record
ord-15d06271e7d0470fb76e8b604810bb64
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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