Morpholine → HCID 58356387, compound

HRID 244612Notes

Reaction equation

HRID 244612 reaction equation
[CH:1]([C:3]1[S:4][C:5]([CH:13]([CH3:15])[CH3:14])=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:14][CH:13]([C:5]1[S:4][C:3]([CH2:1][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:7][C:6]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:15]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58356391HCID 58356391, compound

Product 1

HCID 58356387HCID 58356387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 2-formyl-5-(1-methylethyl)-1,3-thiazole-4-carboxylate (150 mg) was dissolved in anhydrous DCM (10 ml) and morpholine (0.064 ml) was added and the mixture stirred under nitrogen for 2 h at RT. Sodium triacetoxyborohydride (280 mg) was added and the mixture stirred at RT for 18 h. Sodium bicarbonate (20 ml) and DCM (20 ml) were added and separated by hydrophobic frit. The solvent was removed in vacuo and purified by column chromatography on silica gel (10 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound as a yellow oil (77 mg).

Workup

  1. stirringthe mixture stirred at RT for 18 h
  2. customseparated by hydrophobic frit
  3. customThe solvent was removed in vacuo
  4. custompurified by column chromatography on silica gel (10 g silica)
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-06c0d69e06884b71b66f66017d69e0dd
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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