Trifluoroacetic acid → N-Methyl-1-(methylsulfonyl)-3-pyrrolidinamine

HRID 507246Notes

Reaction equation

HRID 507246 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][N:5](CC2C=CC=CC=2)[CH2:4]1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].CCN(C(C)C)C(C)C.C(C(O)=O)(F)(F)F>[Pd].C(Cl)Cl.CCO.CO>[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][N:5]([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:4]1

Participants

10

Reactant 5

HCID 6422Trifluoroacetic acidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 137874781-benzyl-N-methylpyrrolidin-3-amine

Product 1

HCID 59686798N-Methyl-1-(methylsulfonyl)-3-pyrrolidinamine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-(Methylamino)-1-(methanesulfonyl)pyrrolidine was prepared from 3-(methylamino)-1-benzylpyrrolidine after four steps: i) (Boc)2O, MeOH, rt; ii) H2 (1 atm), 10% Pd/C, EtOH; iii) CH3S(O)2Cl, i-Pr2NEt, CH2Cl2; iv) CF3CO2H, CH2Cl2. (m/z): [M+H]+ calcd for C6H14N2O2S: 179.08; found, 179.2. 3R-Methylamino-1-(methanesulfonyl)pyrrolidine was prepared in a similar manner from (3R)-(methylamino)-1-benzylpyrrolidine.

Sources & evidence

ORD record
ord-39676430a78b4800b46ecf5535828819
Source dataset
uspto-grants-2010_08
Patent number
US07786136B2

Reaction notes

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