Benzyl 3-(1,1-dimethylprop-2-en-1-yl)-3-hydroxypyrrolidine-1-carboxylate → 3-(1,1-Dimethylpropyl)pyrrolidin-3-ol

HRID 2275685Notes

Reaction equation

HRID 2275685 reaction equation
[CH3:1][C:2]([C:6]1([OH:21])[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)([CH3:5])[CH:3]=[CH2:4]>CO.[Pd]>[CH3:5][C:2]([C:6]1([OH:21])[CH2:10][CH2:9][NH:8][CH2:7]1)([CH3:1])[CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 66662637Benzyl 3-(1,1-dimethylprop-2-en-1-yl)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 666619013-(1,1-Dimethylpropyl)pyrrolidin-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 3-(1,1-dimethylprop-2-en-1-yl)-3-hydroxypyrrolidine-1-carboxylate (56 mg, 0.00019 mol) was dissolved in methanol and to this solution was added Pd/C (10% dry, 10 mg). The reaction vessel was purged with hydrogen and allowed to stir for 3 h with a hydrogen balloon. The catalyst was filtered off and the filtrate was concentrated in-vacuo to afford the desired product. LCMS (M+H)=158.

Workup

  1. customThe reaction vessel was purged with hydrogen
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated in-vacuo

Sources & evidence

ORD record
ord-1e4caf839f78474b9ddf3d5432d715cf
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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