Ethanolamine → HCID 118107521, compound

HRID 524628Notes

Reaction equation

HRID 524628 reaction equation
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][O:4][CH2:3][C@H:2]1[C:7]([O:9]C)=O.[NH2:18][CH2:19][CH2:20][OH:21]>CO>[OH:21][CH2:20][CH2:19][NH:18][C:7]([C@@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:1]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:9]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 206485414-tert-Butyl 3-methyl (3S)-morpholine-3,4-dicarboxylate

Product 1

HCID 118107521HCID 118107521, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-4-tert-butyl 3-methyl morpholine-3,4-dicarboxylate (0.93 g, 3.8 mmol) and 2-aminoethanol (5 g, 81.9 mmol) in methanol (2 mL) was stirred at 80° C. for 7 hours under N2. The mixture was concentrated in vacuo, diluted with EtOAc (100 mL) and acetic acid (5 mL). The organic layer was washed with brine (80 mL×6), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to give the title compound as a white solid (0.8 g, 77%). The compound was characterized by the following spectroscopic data:

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with EtOAc (100 mL) and acetic acid (5 mL)
  3. washThe organic layer was washed with brine (80 mL×6)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-abcb2849aaa142fb856648ef7a9685e6
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

Loading…