Heptane → HCID 86606005, compound

HRID 1591959Notes

Reaction equation

HRID 1591959 reaction equation
[N:1]1([CH2:6][NH:7][C:8](=[O:18])[CH:9]([CH2:16][CH3:17])[N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([OH:28])(=[O:27])[C@@H:20]([C@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21].CCCCCCC.CCCCCC.C(O)(C)C>CO>[C:24]([C@@H:22]([C@H:20]([C:19]([OH:28])=[O:27])[OH:21])[OH:23])([OH:26])=[O:25].[N:1]1([CH2:6][NH:7][C:8](=[O:18])[C@H:9]([CH2:16][CH3:17])[N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 444305L-Tartaric acidHCID 21585144Isopropanol hexaneHCID 67504785HCID 67504785, compound

Product 1

HCID 86606005HCID 86606005, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3.14 g of N-[(1-pyrrolidinyl)methyl]-α-ethyl-2-oxo-1-pyrrolidineacetamide were suspended in 13 ml of methanol. 1.86 g of L-(+)-tartaric acid were added and it was heated at 60° C. 13 ml of heptane were added to the resulting solution, after which it was left to cool to 40° C. It was seeded with a sample of the compound indicated in the example title to start crystallisation. Then it was slowly cooled to 0-5° C. and maintained at this temperature for 4 hours. The crystallised product was separated by filtration and washed twice over the filter with 1 ml of methanol each time, and finally once with 6 ml of hexane. 2.86 g of the compound indicated in the example title was obtained with a diastereoisomeric excess (d.e.): 69% measured by means of HPLC analysis of the free base with a chiral column (Chiralcel OD, hexane/isopropanol, 220 nm).

Workup

  1. waitafter which it was left
  2. temperatureto cool to 40° C
  3. customcrystallisation
  4. temperatureThen it was slowly cooled to 0-5° C.
  5. temperaturemaintained at this temperature for 4 hours
  6. customThe crystallised product was separated by filtration
  7. washwashed twice over the
  8. filtrationfilter with 1 ml of methanol each time
  9. customwas obtained with a diastereoisomeric excess (d.e.)

Sources & evidence

ORD record
ord-e36c2cc220864de391f6c2dfe1685e8a
Source dataset
uspto-grants-2007_11
Patent number
US07291746B2

Reaction notes

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