Dimethylformamide → 1-{[1-(4-Chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol

HRID 504368Notes

Reaction equation

HRID 504368 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17](O)=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.CN(C)C=O>C(OCC)(=O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([C:17]([N:1]3[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]3)=[O:18])[CH2:15][CH2:16]2)=[CH:12][CH:13]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 982104-HydroxypyrrolidineHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 114999551-{[1-(4-Chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Pyrrolidinol (1.81 g, 0.0208 mol) was added to a mixture of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (3.93 g, 0.0200 mol), benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (8.84 g, 0.0200 mol) and 4-methylmorpholine (9.00 mL, 0.0819 mol) in N,N-dimethylformamide (20.0 mL, 0.258 mol). The mixture was stirred at rt overnight. The mixture was diluted with ethyl acetate (100 mL) and was washed with NaHCO3 (7.5%, 3×30 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was used directly in the next step without further purification.

Workup

  1. washwas washed with NaHCO3 (7.5%, 3×30 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-94cbccb3d5e044428bb20136f51af5ce
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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