1-Octen-3-one → Diethyl 2-(3-hydroxyoctylamino)nonanedioate

HRID 1577792Notes

Reaction equation

HRID 1577792 reaction equation
[NH2:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:19]=[CH:20][C:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[BH4-].[Na+]>C(O)C>[OH:27][CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19][NH:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 613461-Octen-3-oneHCID 4311764Sodium borohydrideHCID 6455180Diethyl 2-aminononane-1,9-dioate

Product 1

HCID 20436863Diethyl 2-(3-hydroxyoctylamino)nonanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl 2-aminononanedioate (10.40 g) and oct-1-en-3-one (5.04 g) were mixed slowly at 0° C., with stirring, and set aside at room temperature for 3 h., giving diethyl 2-(3-oxoctylamino) nonanedioate as a colourless oil, 2.3(4H, multiplet, --CH2 --CO2Et and NCH2CH2CO--), 3.16(1H, triplet, EtO2C--CHR--N), 4.11(2H, quartet, --O--CH2 --CH3), 4.17(2H, quartet, --O--CH2 --CH3). A stirred solution of this ketone (13.5 g) in absolute ethanol (140 ml) was treated dropwise at 0° C. with sodium borohydride (665 ml) in absolute ethanol (70 ml), then kept for 31/2 h. at room temperature, and concentrated at 40° C. in vacuo. The residue dissolved in water, was brought to pH 5 with N hydrochloric acid and extracted throughly with chloroform, the extract was washed with water, dried, and evaporated, giving diethyl 2-(3-hydroxyoctylamino)nonanedioate as a colourless oil.

Workup

  1. customgiving diethyl 2-(3-oxoctylamino) nonanedioate as a colourless oil, 2.3(4H
  2. custom2 h.
  3. customat room temperature
  4. concentrationconcentrated at 40° C. in vacuo
  5. dissolutionThe residue dissolved in water
  6. extractionextracted throughly with chloroform
  7. washthe extract was washed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-527d2b5ed1584240a43b1ee0b57bd9cf
Source dataset
uspto-grants-1981_09
Patent number
US04289707

Reaction notes

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