HCID 66698088, compound → HCID 65419393, compound

HRID 516411Notes

Reaction equation

HRID 516411 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-dd96e9fcbf87440e934dddc8f7724e9b
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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