Potassium Hydroxide → HCID 86729513, compound

HRID 712513Notes

Reaction equation

HRID 712513 reaction equation
Br[CH2:2][CH2:3][O:4][C@H:5]1[C@H:9]([OH:10])[CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1.[OH-].[K+]>CCO>[O:4]1[C@@H:5]2[CH2:6][N:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:8][C@H:9]2[O:10][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86729514HCID 86729514, compound

Product 1

HCID 86729513HCID 86729513, compoundYield 73.33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
85 °C

Procedure

To a solution of (3R,4R)-benzyl 3-(2-bromoethoxy)-4-hydroxypyrrolidine-1-carboxylate (0.20 g, 0.58 mmol) in EtOH (5 mL) was added a solution of KOH (32.0 mg, 0.58 mmol) in EtOH (5 mL). The reaction mixture was stirred for 0.5 h at 85° C., then quenched with water and extracted with CH2Cl2. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 5:1 (v/v)PE/EtOAc) to give the title compound as colorless oil (0.11 g, 73.33%).

Workup

  1. customquenched with water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed with a silica gel column (
  6. washeluting agent

Sources & evidence

ORD record
ord-5fe1325db94446ad9f7f4bee91aba471
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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