1,1'-Carbonyldiimidazole → HCID 67312124, compound

HRID 473563Notes

Reaction equation

HRID 473563 reaction equation
[NH2:1][C@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][C@H:3]1[OH:14].C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>CN(C=O)C>[CH2:7]([N:5]1[CH2:4][C@@H:3]2[C@@H:2]([NH:1][C:20](=[O:21])[O:14]2)[CH2:6]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67310451HCID 67310451, compound

Product 1

HCID 67312124HCID 67312124, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3R,4S)-4-Amino-1-benzylpyrrolidin-3-ol (6 g, 31.4 mmol) in DMF (100 mL) was treated with CDI (5 g, 31.4 mmol) and the reaction mixture was stirred at r.t. for 18 h. The reaction was concentrated in vacuo and azeotroped with heptane. The residual oil was chromatographed on silica with a mixture of dichloromethane and methanol (gradient elution 0-10% methanol), yielding a colourless oil (6 g) which crystallized on standing. δH (DMSO-d6) 7.58 (1H, s), 7.29 (5H, m), 4.96 (1H, dd, J 7.9, 4.5 Hz), 4.16 (1H, dd, J 7.7, 4.9 Hz), 3.59 (2H, m), 3.00 (1H, d, J 11.1 Hz), 2.76 (1H, m), 2.19 (1H, dd, J 11.3, 4.5 Hz), 2.08 (1H, dd, J 10.2, 4.9 Hz).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customazeotroped with heptane
  3. customThe residual oil was chromatographed on silica with a mixture of dichloromethane and methanol (gradient elution 0-10% methanol)

Sources & evidence

ORD record
ord-efd65f69a2384de4892ccceb042c742b
Source dataset
uspto-grants-2014_01
Patent number
US08637491B2

Reaction notes

Loading…