1,2-Dichloroethane → N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-(1-hydroxyethyl)-3-oxocyclopentanecarboxamide

HRID 643543Notes

Reaction equation

HRID 643543 reaction equation
[OH:1][CH:2]([C:4]1([C:10]([OH:12])=O)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)[CH3:3].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.[C:27]([O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:33]=1[CH2:42][NH2:43])([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:34][C:33]=1[CH2:42][NH:43][C:10]([C:4]1([CH:2]([OH:1])[CH3:3])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)=[O:12])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 431536542-Tert-butoxy-5-trifluoromethyl-benzylamineHCID 578805271-(1-Hydroxyethyl)-3-oxocyclopentanecarboxylic acid

Product 1

HCID 59261003N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-(1-hydroxyethyl)-3-oxocyclopentanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 1-(1-hydroxyethyl)-3-oxocyclopentanecarboxylic acid (3.54 g, 20.6 mmol), 1-hydroxy-7-azabenzotriazole (4.14 g, 30.9 mmol), and EDC (5.92 g, 30.9 mmol) in 70 mL of DCM was stirred at rt for 10 min then 1-[2-tert-butoxy-5-(trifluoromethyl)phenyl]methanamine (5.08 g, 20.6 mmol) was added in 10 mL of DCM. The resulting mixture was stirred at rt for 50 min, then was diluted with DCM and washed with water followed by brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by MPLC (silica, 85% ethyl acetate/hexanes) provided N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-(1-hydroxyethyl)-3-oxocyclopentanecarboxamide as a mixture of threo and erythro enantiomer pairs.

Workup

  1. stirringThe resulting mixture was stirred at rt for 50 min
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by MPLC (silica, 85% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4d192067a34d4df8b80b8f72dfcf92a7
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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