Morpholine → HCID 10933213, compound

HRID 1977490Notes

Reaction equation

HRID 1977490 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH:13](/B(O)O)=[CH:14]\[CH2:15][CH2:16][CH2:17][CH3:18]>C(O)C>[O:10]1[CH2:11][CH2:12][N:7]([CH:3](/[CH:13]=[CH:14]/[CH2:15][CH2:16][CH2:17][CH3:18])[C:2]([OH:6])=[O:5])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5326225B-(1E)-1-Hexenylboronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 10933213HCID 10933213, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of glyoxylic acid monohydrate (80 mg, 0.87 mmol) in ethanol (6 mL) was added morpholine (76 mg, 0.87 mmol) in one portion. After 5 min (E)-1-hexenyl boronic acid (121 mg, 0.82 mmol) was added. The reaction mixture was heated at 50° C. for 36 hours, after which time precipitate was isolated by filtration, washed with cold ethanol (10 mL) and dried under vacuum to give (E)-2-morpholino-3-octenoic acid (177 mg,78% yield). 1H-NMR (360 MHz, d6-DMSO) δ 5.65 (dt, J=16.1 Hz, 7.0 Hz, 1H), 5.28 (dd, J=16.1 Hz, 9.1 Hz, 1H), 4.81 (d, J=9.1 Hz, 1H), 2.50 (m, 2H), 1.1 (m, 4H), 0.7 (t, J=7.1 Hz, 3H). 13C-NMR (90 MHz, d6-DMSO) δ 171.1, 136.7, 127.4, 68.8, 62.5, 56.7, 31.7, 30.2, 22.1, 13.9. HRMS-CI (M++1) Calcd for C12H21NO3: 228.1521, Found: 228.1513.

Workup

  1. customafter which time precipitate was isolated by filtration
  2. washwashed with cold ethanol (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-1faacdd1346b401bb05c17cfe3ed4d85
Source dataset
uspto-grants-2001_05
Patent number
US06232467B1

Reaction notes

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