(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine → HCID 59681811, compound

HRID 1394216Notes

Reaction equation

HRID 1394216 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[NH2:12][C:13]1[C:14]([C:18]2[N:19]([CH2:34][CH3:35])[C:20]3[C:25]([C:26](N4C=CN=C4)=[O:27])=[CH:24][N:23]=[CH:22][C:21]=3[N:33]=2)=[N:15][O:16][N:17]=1>CN(C=O)C>[NH2:12][C:13]1[C:14]([C:18]2[N:19]([CH2:34][CH3:35])[C:20]3[C:25]([C:26]([N:1]4[CH2:5][CH2:4][CH2:3][C@H:2]4[CH2:6][N:7]4[CH2:11][CH2:10][CH2:9][CH2:8]4)=[O:27])=[CH:24][N:23]=[CH:22][C:21]=3[N:33]=2)=[N:15][O:16][N:17]=1

Participants

4

Reactant 2

HCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 69158774HCID 69158774, compound

Product 1

HCID 59681811HCID 59681811, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (0.142 g; 0.93 mmol) and the product from Step 1 (0.1 g; 0.31 mmol) in DMF (2 ml) was warmed at 60° C. for 18 h. The cooled mixture was partitioned between water (10 ml) and ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (2×20 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give a colourless gum. The crude material was purified by preparative HPLC using Dynamax C18 column, 8 micron particle size; 250 mm×41.4 mm i.d.; 10-90% acetonitrile/water (0.1% TFA); 70 ml/min; UV detection at 254 nm) to afford the title compound, (0.055 g, 28%); MS (ES+) m/e 411 [M+H]+.

Workup

  1. customThe cooled mixture was partitioned between water (10 ml) and ethyl acetate (3×10 ml)
  2. washThe combined organic extracts were washed with brine (2×20 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a colourless gum
  7. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-230620902fdf469a87d94f81887b52e7
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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