Cyclopentanone → HCID 59286178, compound

HRID 1957984Notes

Reaction equation

HRID 1957984 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1O.C(O[BH-](OC(=O)C)OC(=O)C)(=[O:10])C.[Na+].[C:22]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23]1>ClCCl>[CH:22]1([N:2]2[CH2:6][CH2:5][C@@H:4]([OH:10])[CH2:3]2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 66887889HCID 66887889, compound

Product 1

HCID 59286178HCID 59286178, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(R)-Pyrrolidin-2-ol hydrochloride (0.9 g; 7.31 mmol) was suspended in 50 ml of dichloromethane and sodium triacetoxyborohydride (4.37 g; 0.021 mol) was added. A solution of cyclopentanone (2.75 ml; 0.031 mol) in 530 ml of to dichloromethane was added drop-wise to the reaction mixture. The reaction mixture was maintained at room temperature overnight; it was then diluted with dichloromethane and washed with saturated sodium bicarbonate solution. The water phase was concentrated in vacuo. The crude was treated with dichloromethane in order to separate the salts. The salts were precipitated and filtered. The organic phase concentrated in vacuo. 450 mg (2.90 mmol; 40% yield) of the desired compound were obtained.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. concentrationThe water phase was concentrated in vacuo
  3. additionThe crude was treated with dichloromethane in order
  4. customto separate the salts
  5. customThe salts were precipitated
  6. filtrationfiltered
  7. concentrationThe organic phase concentrated in vacuo

Sources & evidence

ORD record
ord-7c871ca7d847442ba52305f622ce8126
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

Loading…