Morpholine → HCID 58930433, compound

HRID 852915Notes

Reaction equation

HRID 852915 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>ClCCCl.CC(O)=O.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH2:12][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 18617472281232-93-7

Product 1

HCID 58930433HCID 58930433, compoundYield 36.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 42 (950 mg, 4.35 mmol) and morpholine (455 μL, 5.21 mmol) in dry 1,2-dichloroethane (10 mL) at room temperature was added AcOH (2 drops) followed by NaBH(OAc)3 (1.1 g, 5.21 mmol) and the mixture was stirred for 16 h. A solution of 10% K2CO3 was added to the reaction mixture followed by dichloromethane and the phases were separated. The aqueous phase was extracted with CH2Cl2 and organic layer was dried over anhydrous Na2SO4, filtered to form a residue which was purified by flash chromatography on silica gel (EtOAc/CH2Cl2: 20/80) to afford the title compound 43 (460 mg, 1.59 mmol, 36% yield).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with CH2Cl2 and organic layer
  3. dry with materialwas dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customto form a residue which
  6. customwas purified by flash chromatography on silica gel (EtOAc/CH2Cl2: 20/80)

Sources & evidence

ORD record
ord-f958ef7addd6408eaf3f7a75eb9628f5
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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