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

HRID 557975Notes

Reaction equation

HRID 557975 reaction equation
[CH3:1][C:2]([C:6]1([OH:11])[CH2:10][CH2:9][NH:8][CH2:7]1)([CH3:5])[CH2:3][CH3:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:22](O)=[O:23])[CH2:21][CH2:20]2)=[CH:15][CH:14]=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.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2([C:22]([N:8]3[CH2:9][CH2:10][C:6]([C:2]([CH3:1])([CH3:5])[CH2:3][CH3:4])([OH:11])[CH2:7]3)=[O:23])[CH2:20][CH2:21]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 666619013-(1,1-Dimethylpropyl)pyrrolidin-3-ol

Product 1

HCID 666625411-{[1-(4-Chlorophenyl)cyclopropyl]carbonyl}-3-(1,1-dimethylpropyl)pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1,1-Dimethylpropyl)pyrrolidin-3-ol (29.5 mg, 0.000188 mol) was dissolved in DMF and to this solution were added 1-(4-chlorophenyl)cyclopropanecarboxylic acid (44.3 mg, 0.000225 mol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (99.6 mg, 0.000225 mol) and N,N-diisopropylethylamine (49 μL, 0.00028 mol), and the resulting solution was stirred at rt overnight. The product was purified by prep-HPLC. LCMS (M+H)=336

Workup

  1. customThe product was purified by prep-HPLC

Sources & evidence

ORD record
ord-3ccceed83005422a8a225d8646e9dcd6
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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