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Magnesium → 2-[(3,4-Dichloro-5-fluoro-phenyl)-hydroxy-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1895028
Notes
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Reaction equation

HRID 1895028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:9])[C:7]=1[Cl:8].[Mg].[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C:20]1([CH:27]=[O:28])[CH2:24][CH2:25][CH3:26])=[O:18])([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C:20]1([CH:27]([C:4]1[CH:5]=[C:6]([F:9])[C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[OH:28])[CH2:24][CH2:25][CH3:26])=[O:18])([CH3:14])([CH3:15])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 448911995-Bromo-1,2-dichloro-3-fluorobenzeneHCID 866208602-Formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666880302-[(3,4-Dichloro-5-fluoro-phenyl)-hydroxy-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 3,4-dichloro-5-fluorophenyl bromide (1.38 g, 5.66 mmol) and magnesium turnings (0.145 g, 5.94 mmol) in THF (8 mL) was heated at reflux under nitrogen for 30 minutes, then cooled to 0° C. To the reaction mixture was added a solution of 2-formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.682 g, 2.38 mmol) in THE (2 mL) dropwise over 15 minutes. The cold reaction mixture was stirred for one hour, then quenched by the addition of saturated aqueous NH4Cl (20 mL) and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to a yellow oil (1.7 g). Purification by chromatography (silica, 0 to 20% EtOAc in hexanes) gave 2-[(3,4-dichloro-5-fluoro-phenyl)-hydroxy-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.571 g, 1.41 mmol, 50%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 30 minutes
  3. customThe cold reaction mixture
  4. customquenched by the addition of saturated aqueous NH4Cl (20 mL)
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a yellow oil (1.7 g)
  10. customPurification by chromatography (silica, 0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2ff9a211e11543e4b22f55492da93e63
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08513425B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes