Dimethylformamide → 1-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol

HRID 557958Notes

Reaction equation

HRID 557958 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.CN(C)C=O.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([C:23](O)=[O:24])[CH2:22][CH2:21]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.CCN(C(C)C)C(C)C>CCOC(C)=O>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([C:23]([N:1]2[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]2)=[O:24])[CH2:21][CH2:22]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 982104-HydroxypyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7361031-(2,4-Dichlorophenyl)cyclopropanecarboxylic acid

Product 1

HCID 666627281-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-pyrrolidinol (0.861 mL, 0.0106 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) were added 1-(2,4-dichlorophenyl)cyclopropanecarboxylic acid and BOP. After the mixture was stirred for 3 min, DIEA was added. After the reaction mixture was stirred for 3 h, the solution was diluted with AcOEt, washed with sat'd. NaHCO3 aq. (×3), water and brine successively, dried with MgSO4, and concentrated in-vacuo.

Workup

  1. stirringAfter the reaction mixture was stirred for 3 h
  2. washwashed with sat'd
  3. dry with materialNaHCO3 aq. (×3), water and brine successively, dried with MgSO4
  4. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-6a88390baf5c4d1ab1872a442a4c804b
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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