Potassium Iodide → (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-cyclopropylmethylpyrrolidine

HRID 1459639Notes

Reaction equation

HRID 1459639 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(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH:39]1([CH2:42]Br)[CH2:41][CH2:40]1>CC(CC(C)C)=O>[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][N:11]([CH2:42][CH:39]2[CH2:41][CH2:40]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)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine2×

Product 1

HCID 54302406(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-cyclopropylmethylpyrrolidineYield 75.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

(2R,3R,4R)-3,4-Dibenzyloxy-2-benzyloxymethylpyrrolidine (Compound 1) (0.25 g, 0.62 mmol) was dissolved in methyl-isobutylketone (15 ml). Potassium carbonate (0.17 g, 1.2 mmol) and potassium iodide (0.03 g, 0.18 mol) was added. After stirring for 10 min at 25° C. cyclopropylmethylbromide (0.078 ml, 0.81mmol) was added. The mixture was stirred under a N2 atmosphere at 80° C. for 24 hours and evaporated in vacuo. Water (20 ml) was added and extraction with methylene chloride (3×20 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 twice on a silica gel column (1: Eluent: CH2Cl2 /MeOH (19: 1) and 2: Eluent: CH2Cl2 /MeOH (39:1)) gave (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-cyclopropylmethylpyrrolidine (0.213 g, yield: 75%) as an oil.

Workup

  1. additionwas added
  2. customevaporated in vacuo
  3. additionWater (20 ml) was added
  4. extractionextraction with methylene chloride (3×20 ml)
  5. dry with materialdrying of the organic phases with magnesium sulphate and evaporation of the solvent in vacuo
  6. customafforded a yellow oil
  7. customPurification of the crude product twice on a silica gel column (1: Eluent: CH2Cl2 /MeOH (19: 1) and 2: Eluent: CH2Cl2 /MeOH (39:1))

Sources & evidence

ORD record
ord-cb72f35f430c4d3ca78b5707fff1dba4
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

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