(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine → Pyrrolidine, 1-(4-bromobenzoyl)-2-(1-pyrrolidinylmethyl)-, (2S)-

HRID 1676963Notes

Reaction equation

HRID 1676963 reaction equation
O=C1CCC(=O)N1O[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>O1CCCC1>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]([N:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:17])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 138964302,5-Dioxopyrrolidin-1-yl 4-bromobenzoate

Product 1

HCID 11965129Pyrrolidine, 1-(4-bromobenzoyl)-2-(1-pyrrolidinylmethyl)-, (2S)-Yield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 4-bromobenzoic acid-2,5-dioxo-pyrrolidin-1-yl ester (3.5 g, 11.7 mmol) [CAS: 80586-82-9] in tetrahydrofuran (0.15M), is added (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (1.9 mL, 11.7 mmol) and the mixture heated to reflux for 4 h. The reaction is allowed to cool to room temperature and washed with water while extracting with 10% isopropanol/dichloromethane. The organic portion is dried with sodium sulfate, filtered; and concentrated in vacuo. The resulting residue is purified on a silica gel column, eluting with 2M ammonia in methanol and dichloromethane to obtain 2.80 g (71%) of the title compound. MS (ES+) m/e 337.1 (M+1)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h
  3. washwashed with water
  4. extractionwhile extracting with 10% isopropanol/dichloromethane
  5. dry with materialThe organic portion is dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationand concentrated in vacuo
  8. customThe resulting residue is purified on a silica gel column
  9. washeluting with 2M ammonia in methanol and dichloromethane

Sources & evidence

ORD record
ord-c261f1a3fe5740a2bbccad98eea0452e
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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