HCID 66698088, compound → HCID 65419393, compound

HRID 1256570Notes

Reaction equation

HRID 1256570 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][NH:5][S:6]([CH:9]1[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)(=[O:8])=[O:7]>CO.[Pd]>[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][NH:5][S:6]([CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)(=[O:8])=[O:7]

Participants

4

Reactant 1

HCID 66698088HCID 66698088, compound

Product 1

HCID 65419393HCID 65419393, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the above benzyl carbamate (171 mg, 0.481 mmol) and 10% Pd on carbon in MeOH (15 mL) was hydrogenated for 29 hrs. The reaction mixture was filtered through celite, the celite pad was washed with MeOH, and the solvent was removed under vacuum to give N-[2-(dimethylamino)ethyl]-3-pyrrolidinesulfonamide (94 mg, 89%), which was used in the next step without further purification: 1H NMR (DMSO-d6) δ 6.93 (br s, 1H), 3.62 (m, 1H), 3.04-2.99 (m 4H), 2.83 (m, 1H), 2.72 (m, 1H), 2.31 (t, J=6.8 Hz, 2H), 2.14 (s, 6H), 1.92 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite pad was washed with MeOH
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-632c2b1a4e4642819937b3f49f1eedc4
Source dataset
uspto-grants-2013_06
Patent number
US08461158B2

Reaction notes

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