HCID 86713334, compound → HCID 66569359, compound

HRID 928005Notes

Reaction equation

HRID 928005 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C@H:13]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:12][N:11]([C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)[C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86713334HCID 86713334, compound2×

Product 1

HCID 66569359HCID 66569359, compoundYield 115.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (S)-3-(N-benzyloxycarbonyl-N-methylamino)pyrrolidine-1-carboxylate (Intermediate 130, 1.81 g) in trifluoroacetic acid (8 mL) and DCM (8 mL) was left to stand at room temperature for 30 minutes. The resultant mixture was concentrated in vacuo and the residue was dissolved in DCM and brine, basified with 2M sodium hydroxide and filtered through a phase separator. The filtrate was concentrated in vacuo to give benzyl N-methyl-(S)-pyrrolidin-3-ylcarbamate (1.46 g) as a light coloured oil.

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in DCM
  3. filtrationfiltered through a phase separator
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cf5895ddea674dee90de3581593ade40
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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