Sulfuric acid magnesium salt (1:1) → HCID 67054497, compound

HRID 2406228Notes

Reaction equation

HRID 2406228 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[O:16]1[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1.[O-]S([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:23]2[CH2:24][CH2:25][C:20]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:21][CH2:22]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 13936894'-Chlorobiphenyl-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67054497HCID 67054497, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

4′-Chloro-biphenyl-2-carbaldehyde (5.00 g, 23.08 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (4.30 g, 30.0 mmol) were combined in DCE (90 mL) and methanol (68 mL). MgSO4 (˜5 g) was added, and the resulting mixture was stirred for 1 hour at room temperature. Sodium triacetoxyborohydride (14.67 g, 69.2 mmol) was then added, and the reaction was stirred for 16 hours at room temperature. The solvent was removed in vacuo, and the residue was resuspended in CH2Cl2/H2O. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The organic layers were combined, dried over MgSO4, and concentrated. Flash chromatography on silica gel (0-10% NH3 in methanol (˜2M)/CH2Cl2) afforded 8-((4′-chlorobiphenyl-2-yl)methyl)-1,4-dioxa-8-azaspiro[4.5]decane as a brown oil (4.73 g, 60% yield). MS (ESI) m/e (M+H)+: 344.5

Workup

  1. stirringthe reaction was stirred for 16 hours at room temperature
  2. customThe solvent was removed in vacuo
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e7cc5142cee74509b06355683a18e967
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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