Sodium hydride → HCID 67016478, compound

HRID 1891322Notes

Reaction equation

HRID 1891322 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]([CH2:21][OH:22])([CH3:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1>CN(C=O)C>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:10]([CH2:21][O:22][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)([CH3:20])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8170982-Bromo-5-chloropyridineHCID 666532933-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-

Product 1

HCID 67016478HCID 67016478, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of [(3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidin-3-yl]-methanol (4.0 g, 12.7 mmol) in DMF (60 mL) at RT was added NaH (608 mg, 60%, 15.2 mmol). The reaction mixture was heated at 50° C. for 30 minutes, then cooled down to RT before 2-bromo-5-chloropyridine (3.66 g, 19.0 mmol) was added. The resulting brownish solution was stirred overnight at 60° C., then concentrated under high vacuum. The residues was taken up in EtOAc, and washed with water. The organic phase was dried over Na2SO4 and a purification by column chromatography gave 3.90 g (72%) of the title product as a viscous oil. ES-MS m/e: 427.2 (M+H+).

Workup

  1. additionwas added
  2. concentrationconcentrated under high vacuum
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customa purification by column chromatography

Sources & evidence

ORD record
ord-04da5e10f9274a75beb7cfd6600507c3
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

Loading…