Hydrochloric Acid → (3'S)-1'-(4-benzylbenzoyl)-1,3'-bipyrrolidine Hydrochloride

HRID 1163098Notes

Reaction equation

HRID 1163098 reaction equation
[ClH:1].[N:2]1([CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:12]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>C(Cl)Cl.C(N(CC)CC)C>[ClH:1].[CH2:12]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:9]2[CH2:10][CH2:11][C@H:7]([N:2]3[CH2:6][CH2:5][CH2:4][CH2:3]3)[CH2:8]2)=[O:24])=[CH:26][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1364294-Benzylbenzoic acidHCID 2724699PyBOPHCID 146273751-(Pyrrolidin-3-yl)pyrrolidine

Product 1

HCID 68427561(3'S)-1'-(4-benzylbenzoyl)-1,3'-bipyrrolidine Hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of the HCl salt of 3-(pyrrolidino)pyrrolidine (0.44 g, 2.1 mmol) and 4-benzyl benzoic acid (0.34 g, 1.6 mmol) CH2Cl2 is treated sequentially at room temperature with 0.85 mL of triethylamine and solid benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (1.2 g, 2.4 mmol), stirred for 16 h under nitrogen, diluted with CH2Cl2, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo. The concentrate is chromatographically purified. The purified material is treated with ethereal HCl to afford the title compound, identified by H1 NMR and mass spectral analyses.

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe concentrate is chromatographically purified
  5. additionThe purified material is treated with ethereal HCl

Sources & evidence

ORD record
ord-3d7de4344f1a45ad80268e0922f96308
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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