Morpholine → HCID 18948430, compound

HRID 1768590Notes

Reaction equation

HRID 1768590 reaction equation
[O:1]1[CH2:23][CH:2]1[CH2:3][CH:4]([CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CO>[OH:1][CH:2]([CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[CH2:3][CH:4]([CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 18948434HCID 18948434, compound

Product 1

HCID 18948430HCID 18948430, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2 g (6.4 mmole) of t-butyl 4,5-epoxy-2-(1-naphthylmethyl)pentanoate (prepared as described in Preparation 11), 0.84 ml of morpholine and 50 ml of methanol was stirred at room temperature for 6 hours and then allowed to stand overnight. The reaction mixture was then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: a 10 : 90 by volume mixture of methanol and methylene chloride), to afford 1.96 g (76.6%) of the title compound as a pale yellow oil.

Workup

  1. waitto stand overnight
  2. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  3. customThe residue was purified by column chromatography through silica gel (eluent
  4. additiona 10 : 90 by volume mixture of methanol and methylene chloride),

Sources & evidence

ORD record
ord-43ee8faebaf540ffa7f0dfa54021ce2e
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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