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

HRID 2308106Notes

Reaction equation

HRID 2308106 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 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3,4-cis-dimethoxy-pyrrolidine-1-carboxylic acid benzyl ester (16.95 g, 63.88 mmol) in 150 mL MeOH was added 1.3 g Pd on C (10% w/w). 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 product as yellow oil (99% yield). 1H NMR (300 MHz, CDCl3) δ 3.80 (m, 2H), 3.47 (bs, 2H), 3.41 (s, 6H), 3.01 (bs, 2H).

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-37d7e6a7511e4bd8aa9375f6dc6e6d51
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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