HCID 60128540, compound → (3R,4S)-3,4-Dimethoxypyrrolidine

HRID 1825065Notes

Reaction equation

HRID 1825065 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([O:16][CH3:17])[C@H:13]([O:18][CH3:19])[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[CH3:19][O:18][C@H:13]1[C@@H:14]([O:16][CH3:17])[CH2:15][NH:11][CH2:12]1

Participants

4

Reactant 1

HCID 60128540HCID 60128540, compound

Product 1

HCID 20745983(3R,4S)-3,4-DimethoxypyrrolidineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3,4-cis-dimethoxy-pyrrolidine-1-carboxylic acid benzyl ester 5b (16.95 g, 63.9 mmole) in MeOH (150 ml) was added 10% Pd on C (1.3 g). The mixture was stirred under H2 balloon at room temperature for 3 hours and filtered through celite. The filtrate was concentrated, in vacuo, re-dissolved in CH2Cl2 and dried over Na2SO4. The solution was concentrated to give 8.3 g (99%) of a yellow oil. 1H NMR (300 MHz, CDCl3) δ 3.80 (2H, m), 3.47 (2H, bs), 3.41 (6H, s), 3.01 (2H, bs).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated, in vacuo
  3. dissolutionre-dissolved in CH2Cl2
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-a01778b5a9b349cda91194f76f21d881
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

Loading…