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

HRID 481238Notes

Reaction equation

HRID 481238 reaction equation
Cl.[NH2:2][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.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[NH2:2][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 11430Potassium CarbonateHCID 70094840tert-Butyl (S)-5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate hydrochloride

Product 1

HCID 53795147tert-Butyl (S)-5-amino-3,4-dihydro-2H-pyrrole-2-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Amidine hydrochloride 1d (11.0 g, 49.8 mmol) was partitioned between CHCl3 and sat. K2CO3. The layers were separated and the aqueous layer was extracted with CHCl3 (2×). The combined organic phase was dried (Na2SO4) and concentrated to afford 8.50 g (93%) of free base 1e. 1H NMR (300 MHz, CDCl3) δ4.44 (br s, 2H), 4.38 (dd, J=8.0, 5.5, 1H), 2.65-2.42 (m, 2H), 2.32-2.18 (m, 1H), 2.12-2.00 (m, 1H), 1.47 (s, 9H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CHCl3 (2×)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1f3fc0f97d68417db59ed98fa2bac4c2
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

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