Ethanolamine → 2-[(2-Furylmethyl)amino]ethanol

HRID 1964796Notes

Reaction equation

HRID 1964796 reaction equation
[CH:1]1[CH:5]=[C:4]([CH:6]=O)[O:3][CH:2]=1.[NH2:8][CH2:9][CH2:10][OH:11].C[C@H](NC([C@H]1N(C([C@@H](NC([C@@H](N)CC2C=CC(O)=CC=2)=O)CC(O)=O)=O)CCC1)=O)C(N1[C@H](C(N2[C@H](C(N3[C@H](C(N4[C@H](C(N5[C@H](C(N6[C@H](C(O)=O)CCC6)=O)CCC5)=O)CCC4)=O)CCC3)=O)CCC2)=O)CCC1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[O:3]1[CH:2]=[CH:1][CH:5]=[C:4]1[CH2:6][NH:8][CH2:9][CH2:10][OH:11]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 7362FurfuralHCID 5049666Sodium triacetoxyborohydrideHCID 5488810Peptide oostatic hormone

Product 1

HCID 47226102-[(2-Furylmethyl)amino]ethanol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

An aldehyde, e.g., 2-furfuraldehyde (2 g, 20.82 mmol), and an amine, e.g., 2-aminoethanol, (1.65 g, 27.06 mmol) were poured together in a mixture 1:1 TMOF:DCE (50 ml) and the reaction mixture was cooled down to zero degree. The reducing agent NaBH(OAc)3 (6.18 g, 29.14 mmol) was added in 4 subsequent portions over a 5 min period, the reaction mixture was allowed to gradually warm to room temperature and stirred for 16 hours. The solvents was removed from the reaction in vacuo and the residue was partitioned between dichloromethane (150 ml) and saturated bicarbonate solution (50 ml). After separation, the organic layer was washed with saturated bicarbonate solution (50 ml) and brine (50 ml). The combined organic layers were then dried over sodium sulphate, filtered and the solvent removed in vacuo. The desired secondary amines, e.g., 2-[(2-furylmethyl)amino]ethanol, were obtained as a yellowish oil (1.82 g, 62%).

Workup

  1. customThe solvents was removed from the reaction in vacuo
  2. customthe residue was partitioned between dichloromethane (150 ml) and saturated bicarbonate solution (50 ml)
  3. customAfter separation
  4. washthe organic layer was washed with saturated bicarbonate solution (50 ml) and brine (50 ml)
  5. dry with materialThe combined organic layers were then dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9be17ea6be714fdbbf3333201b4abd9a
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

Loading…