Hydrochloric Acid → HCID 66589983, compound

HRID 2363561Notes

Reaction equation

HRID 2363561 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][C@H:4]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:5]([O:7]C(C)(C)C)=[O:6].[ClH:19]>O1CCOCC1>[ClH:19].[CH3:1][CH:2]([CH3:18])[CH2:3][C@H:4]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66590793HCID 66590793, compound

Product 1

HCID 66589983HCID 66589983, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-020e6a227521460bbf4f5dba37c2671c
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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