Water → Isopropyl 5-(2-aminoethyl)thiophene-2-carboxylate

HRID 1528015Notes

Reaction equation

HRID 1528015 reaction equation
O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:21]([CH2:24][CH2:25][C:26]1[S:30][C:29]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[CH:28][CH:27]=1)=[N+]=[N-]>C1COCC1>[NH2:21][CH2:24][CH2:25][C:26]1[S:30][C:29]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57487064Isopropyl 5-(2-azidoethyl)thiophene-2-carboxylate

Product 1

HCID 57487046Isopropyl 5-(2-aminoethyl)thiophene-2-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Water (0.1 mL) and triphenylphosphine (288 mg, 1.1 mmol) were added sequentially to a solution of the azide from step 3 (239 mg, 1.0 mmol) in THF (2.0 mL) and the reaction was stirred at room temperature overnight. The solvent was removed under a stream of nitrogen and then 1.0 N aqueous HCl (7.5 mL) was added. The mixture was extracted with EtOAc (2×5 mL). The aqueous phase was basified with 2.0 M aqueous NaOH (5 mL). The mixture was extracted with EtOAc (3×10 mL) and these extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 175 mg (82%) of the title compound.

Workup

  1. customThe solvent was removed under a stream of nitrogen
  2. addition1.0 N aqueous HCl (7.5 mL) was added
  3. extractionThe mixture was extracted with EtOAc (2×5 mL)
  4. extractionThe mixture was extracted with EtOAc (3×10 mL)
  5. dry with materialthese extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1eae54c83d884c67a7bb87ab9dc0a732
Source dataset
uspto-grants-2015_07
Patent number
US09090584B2

Reaction notes

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