Magnesium monoxide → (2S,4S)-1-tert-butyl 2-methyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

HRID 1504336Notes

Reaction equation

HRID 1504336 reaction equation
[CH3:1][O:2]/[CH:3]=[C:4]1\[CH2:5][C@@H:6]([C:16]([O:18][CH3:19])=[O:17])[N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]\1.[O-2].[Mg+2].[H][H]>[Pd].CO>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1

Participants

6

Reactant 3

HCID 6850729Magnesium monoxideHCID 86682810(S,E)-1-tert-butyl 2-methyl 4-(methoxymethylene)pyrrolidine-1,2-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 69675330(2S,4S)-1-tert-butyl 2-methyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (5,E)-1-tert-butyl 2-methyl 4-(methoxymethylene)pyrrolidine-1,2-dicarboxylate (9 g, 33.21 mmol), magnesium oxide (12 g, 33.21 mmol) and palladium on carbon (3 g) in methanol (100 mL) was held under a steady flow of hydrogen at RT for 2 h, and filtered. The organic phase was concentrated to provide the title intermediate (9 g, 100% yield) as a colorless oil. 1H NMR (400 MHz, (CD3)2S═O): δ(ppm) 1.367 (s, 9H), 1.620-1.670 (m, 1H), 1.904-1.953 (m, 1H), 3.110-3.140 (s, 3H, J=12 Hz), 3.255-3.360 (m, 2H), 3.523-3.561 (m, 1H), 3.653 (s, 3H), 4.241-4.283 (m, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-91c122b1aa8e45889965ef199884e6c7
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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