Morpholine → HCID 58105210, compound

HRID 1668514Notes

Reaction equation

HRID 1668514 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH2:16][CH2:17][C:18]([OH:20])=O)[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH2:16][CH2:17][C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58105226HCID 58105226, compound

Product 1

HCID 58105210HCID 58105210, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3-[6-(t-Butyldimethylsilanyloxymethyl)pyridin-2-yl]-propionic acid (1.65 g) was dissolved in 20 mL of methylene chloride, and 584 μL of morpholine, 1.6 g of WSC and 1.56 mL of triethylamine were added to the solution, and then the mixture was stirred at room temperature overnight. The reaction mixture was diluted with chloroform, transferred into a separating funnel, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (chloroform-methanol=30:1) to give 1.91 g of 3-[6-(t-butyldimethylsilanyloxymethyl)pyridin-2-yl]-1-morpholin-4-yl-propan-1-one as a yellow oil.

Workup

  1. customtransferred into a separating funnel
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (chloroform-methanol=30:1)

Sources & evidence

ORD record
ord-29c57a8e7bf3467797acf32b86c84148
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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