Hydrochloric Acid → HCID 67017460, compound

HRID 81396Notes

Reaction equation

HRID 81396 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)[CH:5]=[CH:6][CH:7]=1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][NH:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86658662HCID 86658662, compound

Product 1

HCID 67017460HCID 67017460, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

920 mg of tert-butyl (R)-2-{[(3-fluorophenyl)methylamino]methyl}pyrrolidine-1-carboxylate are dissolved in, 10 ml of THF, and 5 ml of ethanolic hydrochloric acid are added. The mixture is stirred at 80° C. for 4 h and, for work-up, partitioned between 50 ml of water and 50 ml of ethyl acetate at room temperature. Conventional work-up and purification by chromatography on silica gel gives 300 mg of (3-fluorophenyl)methyl-(R)-1-pyrrolidin-2-ylmethylamine; Rt.: 1.377 min; [M+H]+209.2.

Workup

  1. additionare added
  2. custompartitioned between 50 ml of water and 50 ml of ethyl acetate at room temperature
  3. customConventional work-up and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-9ae960b6b46b4c6b8adf2f6155b6a944
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

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