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6-Bromo-2,3-dichloropyridine → 2-[(5,6-Dichloro-pyridin-2-yl)-hydroxy-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661549
Notes
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Reaction equation

HRID 661549 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[N:3]=1.C([Mg]Cl)(C)C.[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C:23]1([CH:30]=[O:31])[CH2:27][CH2:28][CH3:29])=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C:23]1([CH:30]([C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[N:3]=1)[OH:31])[CH2:27][CH2:28][CH3:29])=[O:21])([CH3:17])([CH3:18])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 467368346-Bromo-2,3-dichloropyridineHCID 866208602-Formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418918HCID 178418918, compound

Product 1

HCID 866208612-[(5,6-Dichloro-pyridin-2-yl)-hydroxy-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Procedure

To a stirred solution of 2-bromo-5,6-dichloro-pyridine (0.500 g, 2.20 mmol) in THF (6 mL) at 0° C. and under nitrogen was added isopropylmagnesium chloride (1.21 mL of a 2 M solution in THF, 2.42 mmol) dropwise. After 2 hours, a solution of 2-formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.317 g, 1.32 mmol) in THF (1 mL) was added to the reaction mixture dropwise. After 30 minutes, the reaction mixture was warmed to ambient temperature and stirred for one hour, then quenched by the addition of saturated aqueous NH4Cl (10 mL) and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification of the residue by chromatography (silica, 0 to 40% EtOAc in hexanes) gave 2-[(5,6-dichloro-pyridin-2-yl)-hydroxy-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.289 g, 0.745 mmol, 56%) as a yellow oil and as an inseparable mixture of diastereomers.

Workup

  1. waitAfter 30 minutes
  2. customquenched by the addition of saturated aqueous NH4Cl (10 mL)
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by chromatography (silica, 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-883913b88e624e9b905debdb5b22015d
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084623B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes