Methanol → Benzyl (S)-4-amino-3,3-dimethylpyrrolidine-1-carboxylate

HRID 877708Notes

Reaction equation

HRID 877708 reaction equation
[NH2:1][CH:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4][C:3]1([CH3:18])[CH3:17].CO>C(=O)=O>[NH2:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4][C:3]1([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 887MethanolHCID 66936024Benzyl 4-amino-3,3-dimethylpyrrolidine-1-carboxylate2×

Product 1

HCID 68350392Benzyl (S)-4-amino-3,3-dimethylpyrrolidine-1-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

(+/−)-Benzyl 4-amino-3,3-dimethylpyrrolidine-1-carboxylate (Intermediate 11, 0.48 g was resolved via chiral SFC chromatography under the following conditions: column OD-H (0.46×25 cm), 20% MeOH with 0.1% DEA in CO2, 3 mL/min, 40° C., 140 bars. The second fraction was concentrated to afford the title compound (S)-benzyl 4-amino-3,3-dimethylpyrrolidine-1-carboxylate (0.2 g, 42% yield).

Workup

  1. custom3 mL/min, 40° C., 140 bars
  2. concentrationThe second fraction was concentrated

Sources & evidence

ORD record
ord-8302bc76a4e540819f6549868bf5abf1
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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