Morpholine → Benzyl (1r)-1-(hydroxymethyl)-3-(4-morpholinyl)-3-oxopropylcarbamate

HRID 731553

Reaction equation

HRID 731553 reaction equation
[O:1]=[C:2]1[O:6][CH2:5][C@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>O1CCOCC1>[OH:6][CH2:5][C@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:2]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:1]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

Product 1

HCID 59186710Benzyl (1r)-1-(hydroxymethyl)-3-(4-morpholinyl)-3-oxopropylcarbamateYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of EXAMPLE 21B (13.5 g, 57.4 mmol) and morpholine (10.0 mL, 115 mmol) in dioxane (100 mL) was stirred at 70° C. for 18 hours. The solution was concentrated and purified by silica gel chromatography eluting with 10% methanol/ethyl acetate to provide the desired product 6.0 g, 86%).

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by silica gel chromatography
  3. washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-bff9c613403b4e95be6fe0c912eb22be
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Linked notes

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