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

HRID 969169Notes

Reaction equation

HRID 969169 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-d8c13e81d5b34eb29cd3ec806b73e46f
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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