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

HRID 481237Notes

Reaction equation

HRID 481237 reaction equation
CS[C:3]1[CH2:4][CH2:5][C@@H:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:7]=1.[NH4+:15].[Cl-:16]>CO>[ClH:16].[NH2:15][C:3]1[CH2:4][CH2:5][C@@H:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 70094840tert-Butyl (S)-5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate hydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1c (10.17 g, 47.2 mmol) in 100 mL MeOH, was added NH4Cl (2.65 g, 49.6 mmol). The mixture was refluxed for 2 h, then concentrated. The residue was taken up in 200 mL CHCl3 and stirred for 20 min until only a fine suspension persisted. The mixture was filtered and the filtrate concentrated. The solid was suspended in hexanes, sonicated, and then filtered and dried to afford 8.30 g (80%) of 1d as an off-white solid. 1H NMR (300 MHz, CDCl3) δ4.44 (dd, J=8.8, 5.1, 1H), 3.11-3.05 (m, 2H), 2.58-2.45 (m, 1H), 2.28-2.15 (m,1H), 1.48 (s, 9H).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. concentrationconcentrated
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated
  5. customsonicated
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-bc1625331e264be492090702a9c22a96
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

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