Ammonia → 3-Hydroxy-4-aminocarbonyl-1-phenylmethyl pyrrolidine

HRID 1089217Notes

Reaction equation

HRID 1089217 reaction equation
[OH:1][CH:2]1[CH:6]([C:7](OCC)=[O:8])[CH2:5][N:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3]1.[NH3:19]>CO>[OH:1][CH:2]1[CH:6]([C:7]([NH2:19])=[O:8])[CH2:5][N:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 143477863-Hydroxy-4-ethyloxycarbonyl-1-phenylmethyl pyrrolidine

Product 1

HCID 148395853-Hydroxy-4-aminocarbonyl-1-phenylmethyl pyrrolidineYield 22.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 11.0 g (44.0 mmol) of 3-hydroxy-4-ethyloxycarbonyl-1-phenylmethyl pyrrolidine (prepared according to E. Jaeger and J. H. Biel in J. Org. Chem. 1965, 30, (740) in 40 g of 25% ammonia in methanol was heated at 100° C. under pressure overnight. The solution was cooled and evaporated to dryness. The oily residue was purified by chromatography using dichloromethane-methanol (85:15) to yield 2.14 g (22%) of the title compound. M.P. 128° C.

Workup

  1. temperatureThe solution was cooled
  2. customevaporated to dryness
  3. customThe oily residue was purified by chromatography

Sources & evidence

ORD record
ord-2acea5aa25c548ce972bc4db1164e05d
Source dataset
uspto-grants-1990_10
Patent number
US04965273

Reaction notes

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