Morpholine → HCID 58932632, compound

HRID 1786441Notes

Reaction equation

HRID 1786441 reaction equation
[OH:1][C@@H:2]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[CH3:19][C:16]([CH3:17])([CH3:18])[CH2:15][C@H:2]([OH:1])[CH2:3][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 58932631HCID 58932631, compound

Product 1

HCID 58932632HCID 58932632, compoundYield 67%

Conditions

Temperature
160 °C

Procedure

(S)-toluene-4-sulfonic acid 2-hydroxy-4,4-dimethyl-pentyl ester obtained from Example 4, step A (700 mg, 2.4 mmol) was charged to a large microwave reactor vial and treated with morpholine (3 mL). The vial was crimped shut and heated to 160° C. for 6 minutes. The solvent was then removed. The resulting oil was dissolved in ethyl acetate and extracted 3 time with aqueous 1 M HCl. The organics were discarded and the aqueous layer was made basic with solid NaOH and extracted 3 times with ethyl acetate. The organic extracts were combined, dried over MgSO4 and the solvent was removed to afford 330 mg (67%) of material which was used without further purification: HPLC-MS calcd. for C11H23NO2 (M+H+) 202.2, found 202.5.

Workup

  1. customThe solvent was then removed
  2. dissolutionThe resulting oil was dissolved in ethyl acetate
  3. extractionextracted 3 time with aqueous 1 M HCl
  4. extractionextracted 3 times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-fb86566308fe4d67b8cb99760354a6ee
Source dataset
uspto-grants-2009_03
Patent number
US07507755B2

Reaction notes

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