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

HRID 2275619Notes

Reaction equation

HRID 2275619 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-6de5960553ed49179cd8350abcc64177
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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