Morpholine → HCID 11610965, compound

HRID 1516147Notes

Reaction equation

HRID 1516147 reaction equation
[CH3:1][O:2][C:3](=[O:24])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=O)[CH:17]=1)=[CH:5]/[O:6][CH3:7].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[CH:17]=1)=[CH:5]/[O:6][CH3:7]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14857823HCID 14857823, compound

Product 1

HCID 11610965HCID 11610965, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

326 mg (1.0 mmol) of the compound obtained in Step 1 was dissolved in 5 ml of methylene chloride, and 297 mg (1.4 mmol) of NaBH(OAc)3 and 87 μl (1.0 mmol) of morpholine were added thereto. After stirring at room temperature for 4 hours, the reaction mixture was treated with a saturated sodium bicarbonate aqueous solution, and the water layer was separated, and extracted twice with 20 ml portions of methylene chloride. The organic layers were combined, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The residue was subjected to column chromatography using 3% methanol/chloroform as an eluent to obtain 385 mg (yield 97%) of (E)-methyl-2-[2-((3-(morpholinomethyl)phenoxy)methyl)phenyl]-3-methoxyacrylate as an oil.

Workup

  1. customthe water layer was separated
  2. extractionextracted twice with 20 ml portions of methylene chloride
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-88a56b601fad403da1e7b32b14fd9a0e
Source dataset
uspto-grants-2012_07
Patent number
US08227456B2

Reaction notes

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