Ammonium Chloride → tert-Butyl (S)-5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 1737851Notes

Reaction equation

HRID 1737851 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[N:12]=[C:11](SC)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+:15].[Cl-]>CO>[C:1]([O:5][C:6]([C@H:8]1[N:12]=[C:11]([NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 53965507tert-Butyl (S)-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Product 1

HCID 53795147tert-Butyl (S)-5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-2-methylsulfanyl-3,4-dihydro-5H-pyrrole-5-carboxylic acid t-butyl ester (0.42 g, 1.95 mmol) in 4.0 mL anhydrous MeOH was added anh NH4Cl (0.11 g, 2.05 mmol). The reaction mixture was heated to reflux for 2 h, concentrated in vacuo, and the residue was taken up in CH2C2. The white solids were filtered, and the filtrate was concentrated to provide (S)-2-amino-3,4-dihydro-5H-pyrrole-5carboxylic acid t-butyl ester.HCl (0.41 g, 94%) as a light yellow solid 1H NMR (CDCl3) δ 1.49 (s, 9H), 2.24 (m, 1H), 2.52 (m, 1H), 3.06-3.08 (m, 2H), 4.44 (m, 1H), 9.81-9.8 (m, 2H). MS calcd for C9H16N2O2 +H 185, found 185.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. filtrationThe white solids were filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6af4239c47d8489887b4e1512427ce1c
Source dataset
uspto-grants-1999_10
Patent number
US05962487

Reaction notes

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