Diisopropylethylamine → Rac-(3-hydroxymethyl-pyrrolidin-1-yl)-[5-methanesulfonyl-2-((s)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

HRID 552687Notes

Reaction equation

HRID 552687 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[NH:52]1[CH2:56][CH2:55][CH:54]([CH2:57][OH:58])[CH2:53]1>CN(C)C=O>[OH:58][CH2:57][CH:54]1[CH2:55][CH2:56][N:52]([C:10]([C:9]2[CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=2[O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[O:12])[CH2:53]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13400657(Pyrrolidin-3-yl)methanolHCID 58863351(S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acid

Product 1

HCID 59030469Rac-(3-hydroxymethyl-pyrrolidin-1-yl)-[5-methanesulfonyl-2-((s)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.01 mol 5-Methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (CAS: 845616-82-2) in 40 ml N,N-dimethylformamide were added successively 3.57 g TBTU, 8.5 ml N-ethyldiisopropylamine and 1 g rac-pyrrolidin-3-yl-methanol (CAS: 5082-74-6). The reaction mixture was stirred at room temperature for 16 h and then concentrated in vacuo. The mixture was taken in ethyl acetate and washed twice with water and twice with saturated NaHCO3. The organic phase was dried over Na2SO4 and filtered. The solvent was evaporated. The crude oil was purified on silica gel (eluent: ethyl acetate) to yield the title compound as an off white foam. MS (m/e): 396.1 (M+H+, 100%).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed twice with water and twice with saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customThe crude oil was purified on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-608f51b652a742d19cae1ca85fb388fa
Source dataset
uspto-grants-2011_05
Patent number
US07951836B2

Reaction notes

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