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

HRID 985193Notes

Reaction equation

HRID 985193 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) δ3.80 (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-d4b4edb95fc641c593a69191a2eb1c38
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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