Potassium Carbonate → HCID 66590793, compound

HRID 2363560Notes

Reaction equation

HRID 2363560 reaction equation
[NH2:1][C@@H:2]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][O:23][CH2:24][CH2:25]Br>C(#N)C>[CH3:12][CH:11]([CH3:13])[CH2:10][C@H:2]([N:1]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoate

Product 1

HCID 66590793HCID 66590793, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

(S)-tert-Butyl 2-amino-4-methylpentanoate (1.0042 g, 5.36 mmol), potassium carbonate (2.446 g, 17.69 mmol), and 1-bromo-2-(2-bromoethoxy)ethane (1.368 g, 5.90 mmol) were combined in acetonitrile (30 mL). The reaction was heated at 80° C. overnight. The reaction was cooled and filtered and the solvent removed in vacuo. The crude material was purified by silica gel chromatography using 5-50% ethyl acetate/hexanes to give (S)-tert-butyl 4-methyl-2-morpholinopentanoate: 1H NMR (300 MHz, CDCl3) δ ppm 3.76-3.58 (m, 4H), 3.11 (dd, J=6.9, 8.1, 1H), 2.74-2.53 (m, 4H), 1.71-1.55 (m, 2H), 1.51-1.34 (m, 10H), 0.92 (dd, J=6.6, 7.3, 6H). (S)-tert-Butyl 4-methyl-2-morpholinopentanoate (0.637 g, 2.475 mmol) and 4 N hydrochloric acid in dioxane (5 mL) were combined. The reaction mixture was stirred at ambient temperature for 24 hours, then the solvent removed in vacuo to give (S)-4-methyl-2-morpholinopentanoic acid hydrochloride: MS (DCI+) m/z 202 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-feaafd5c1ffd469eb5b018c0a0e6c310
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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