Benzyl (3S)-3-[(tert-butoxycarbonyl)(methyl)amino]-3-methylpyrrolidine-1-carboxylate → tert-Butyl methyl[(3S)-3-methylpyrrolidin-3-yl]carbamate

HRID 17635Notes

Reaction equation

HRID 17635 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:25])[C@@:9]1([CH3:24])[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[OH-].[Pd+2].[OH-]>[CH3:25][N:8]([C@@:9]1([CH3:24])[CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 51041898Benzyl (3S)-3-[(tert-butoxycarbonyl)(methyl)amino]-3-methylpyrrolidine-1-carboxylate

Product 1

HCID 51041899tert-Butyl methyl[(3S)-3-methylpyrrolidin-3-yl]carbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Benzyl (3S)-3-[(tert-butoxycarbonyl)(methyl)amino]-3-methylpyrrolidine-1-carboxylate (I-347) (367 mg, 1.05 mmol) was dissolved in 1,4-dioxane (10 ml), then palladium hydroxide catalyst (37 mg) was added, followed by stirring under hydrogen atmosphere at room temperature for 5 hours. The reaction liquid was filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product of the entitled compound. This was used in the next reaction as such.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-64015c073a5e4785a9cfb4acd54adf2b
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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