Sodium Sulfate → HCID 178491122, compound

HRID 1631443Notes

Reaction equation

HRID 1631443 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH4-].[Na+]>ClCCl.CO.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 312444-MethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 178419079HCID 178419079, compound

Product 1

HCID 178491122HCID 178491122, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 24840Magnesium perchlorateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of tert-butyl (trans)-4-aminocyclohexylcarbamate (1.0 g, 4.67 mmol) in dichloromethane (30 mL) was treated with 4-methoxybenzaldehyde (0.568 mL, 4.67 mmol) and magnesium perchlorate (0.052 g, 0.233 mmol) and stirred at room temperature overnight. A large excess of solid Na2SO4 was added, and the reaction mixture was stirred for 1 h., filtered, and the filter cake was rinsed with MeOH. The filtrate and rinse were combined and concentrated to yield a white solid, which was dissolved in MeOH (10 mL). This solution was treated with NaBH4 (0.265 g, 7.00 mmol) in a single portion. The reaction mixture became a light yellow solution which was stirred at room temperature for 1.5 h. The reaction was quenched with 1.0N NaOH, diluted with water (150 mL), and stirred for 30 min. The resulting white solid was collected by filtration, washed with water, and air dried to provide 15A (1.26 g, 81% yield). MS (ES): m/z=335 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.20 (d, 2H, J=8.5 Hz); 6.83 (d, 2H, J=8.5 Hz); 6.63 (d, 1H, J=8.0 Hz); 3.70 (s, 2H); 3.60 (br. s, 1H); 3.31 (s, 3H); 3.08-3.18 (m, 1H); 2.06-2.25 (m, 1H); 1.65-1.88 (m, 4H); 1.34 (s, 9H); 0.93-1.12 (m, 4H).

Workup

  1. stirringthe reaction mixture was stirred for 1 h.
  2. filtrationfiltered
  3. washthe filter cake was rinsed with MeOH
  4. washThe filtrate and rinse
  5. concentrationconcentrated
  6. customto yield a white solid, which
  7. stirringwas stirred at room temperature for 1.5 h
  8. customThe reaction was quenched with 1.0N NaOH
  9. additiondiluted with water (150 mL)
  10. stirringstirred for 30 min
  11. filtrationThe resulting white solid was collected by filtration
  12. washwashed with water, and air
  13. customdried

Sources & evidence

ORD record
ord-cc0c5818d2c5475e8c1af64ed1952cc7
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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