Morpholine → HCID 54129992, compound

HRID 1656693Notes

Reaction equation

HRID 1656693 reaction equation
C([O:5][C:6](=[O:14])[C@H:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[NH2:8])C1OC1.N1CC[O:18]CC1>>[OH:18][O:5][C:6](=[O:14])[C@H:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[NH2:8]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 53994349HCID 53994349, compound

Product 1

HCID 54129992HCID 54129992, compoundYield 220.5%

Procedure

To a solution of 712 mg (1.81 mmol) of glycidyl ester 28 and 0.316 mL (3.62 mmol, 2.0 equiv) of morpholine was added 1 g of neutral alumina. The reaction mixture was stirred overnight and then filtered and concentrated. Purification by flash chromatography (30×150 mm silica gel, 200 mL of 1.5% and 200 mL of 2.5% methanol/dichloromethane) provided 651 mg (75%) of the title compound: 1H NMR (300 MHz, CD3OD) δ7.38-7.29 (m, 5H), 5.09 (s, 2H), 4.19-3.97 (m, 3H), 3.69-3.60 (m, 5H), 2.56-2.41 (m, 8H), 2.22-2.08 (m, 1H), 1.97-1.84 (m, 1H), 1.45 (s, 9H); MS(FAB) 481 (M+1), 425.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification by flash chromatography (30×150 mm silica gel, 200 mL of 1.5% and 200 mL of 2.5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7197328e157f48e8a07ffddcb9727818
Source dataset
uspto-grants-1993_10
Patent number
US05254682

Reaction notes

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