Potassium Iodide → (2R,3R,4R)-1-allyl-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine

HRID 1280804Notes

Reaction equation

HRID 1280804 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][NH:11][C@@H:10]1[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[I-].[K+].[CH3:40][C:41]([CH2:43]C(C)C)=O>>[CH2:43]([N:11]1[CH2:12][C@@H:13]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:10]1[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:41]=[CH2:40]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 7909Methyl Isobutyl KetoneHCID 8471TriethylamineHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine2×

Product 1

HCID 54476962(2R,3R,4R)-1-allyl-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidineYield 81%

Conditions

Temperature
80 °C

Procedure

(2R,3R,4R)-3,4-Dibenzyloxy-2-benzyloxymethylpyrrolidine (Compound 1) (1.025 g, 2.5 mmol) was dissolved in methylisobutylketone (15 ml). Triethylamine (0.53 ml, 3.8 mmol) and potassium iodide (0.04 g) were added. The mixture was stirred under a nitrogen atmosphere for 4 hours at 80° C. and 24 hours at room temperature and evaporated in vacuo. Water (40 ml) was added and extraction with methylene chloride (3×40 ml), drying of the organic phases with magnesium sulphate and evaporation of the solvent in vacuo afforded a yellow oil. Purification of the crude product on a silica gel column (Eluent: Heptane/ethyl acetate (9:1)) gave (2R,3R,4R)-1-allyl-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (0.91 g, yield: 81%) as an oil.

Workup

  1. customevaporated in vacuo
  2. additionWater (40 ml) was added
  3. extractionextraction with methylene chloride (3×40 ml)
  4. dry with materialdrying of the organic phases with magnesium sulphate and evaporation of the solvent in vacuo
  5. customafforded a yellow oil
  6. customPurification of the crude product on a silica gel column (Eluent: Heptane/ethyl acetate (9:1))

Sources & evidence

ORD record
ord-13d53f8165034d8aa734538f5f57e96d
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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