Pyrrolidine → HCID 54196280, compound

HRID 1815445Notes

Reaction equation

HRID 1815445 reaction equation
[C:1]12([C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]OS(C3C=CC(C)=CC=3)(=O)=O)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>C(#N)C>[N:31]1([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11]([C:1]23[CH2:8][CH:7]4[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]4)[CH2:2]2)[CH2:10]3)=[O:12])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 54239756HCID 54239756, compound

Product 1

HCID 54196280HCID 54196280, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an ice-cooled solution of the product from step b in acetonitrile (25 ml) was added pyrrolidine (6.41 ml, 76.8 mmol). The coolant was removed and the reaction mixture was stirred at ambient temperature for 20 h. The mixture was partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous phase was discarded and the organic phase extracted with aqueous 2M hydrochloric acid (100 ml). The organic phase was discarded and the aqueous phase was washed with further ethyl acetate (50 ml). The pH of the aqueous phase was adjusted to pH 11 and then extracted twice with chloroform (100 ml). The combined organic phases were washed with brine (100 ml) and dried over anhydrous magnesium sulfate. The filtrate was evaporated at reduced pressure to afford the title compound (4.34 g, 100%). 1H NMR 5.54 (1H, br s), 3.26-3.20 (2H, m), 2.50-2.40 (6H, m), 2.05 (3H, s), 1.85-1.73 (14H, m), 1.52-1.50 (4H, m), 1.36-1.33 (4H, m).

Workup

  1. customThe coolant was removed
  2. customThe mixture was partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. extractionthe organic phase extracted with aqueous 2M hydrochloric acid (100 ml)
  4. washthe aqueous phase was washed with further ethyl acetate (50 ml)
  5. extractionextracted twice with chloroform (100 ml)
  6. washThe combined organic phases were washed with brine (100 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-c4a287705c2a48b1a057d2041471105f
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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