tert-Butyl (3-aminopropyl)carbamate → HCID 86718594, compound

HRID 1480632Notes

Reaction equation

HRID 1480632 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:13]([C:17]1[CH:18]=[C:19]([C:26]2[CH:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=2)[C:20]([OH:25])=[C:21]([CH:24]=1)[CH:22]=O)([CH3:16])([CH3:15])[CH3:14].[BH4-].[Na+]>CO>[C:13]([C:17]1[CH:18]=[C:19]([C:26]2[CH:27]=[N:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=2)[C:20]([OH:25])=[C:21]([CH:24]=1)[CH2:22][NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 4311764Sodium borohydrideHCID 86718581HCID 86718581, compound

Product 1

HCID 86718594HCID 86718594, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl N-(3-aminopropyl)carbamate (0.404 g, 2.32 mmol) was added to a solution of 5-(tert-butyl)-2-hydroxy-3-(6-(trifluoromethyl)pyridin-3-yl)benzaldehyde (from Example 47 Step 1) (0.5 g, 1.55 mmol) in methanol (5 mL) and the reaction mixture stirred at room temperature under nitrogen for 4 hours. Sodium borohydride (234 mg, 6.19 mmol) was then added and the reaction mixture stirred at room temperature for 2.5 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (5 mL), the mixture stirred vigorously for 10 minutes then partitioned between ethyl acetate (80 mL) and saturated aqueous ammonium chloride solution (80 mL). The organic phase was separated, washed with water (80 mL) and saturated brine (80 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a yellow syrup. The product was purified using flash chromatography on silica eluting with a solvent gradient of 0 to 6% methanol (containing 1% aqueous ammonium hydroxide) in dichloromethane to give tert-butyl (3-((5-(tert-butyl)-2-hydroxy-3-(6-(trifluoromethyl)pyridin-3-yl)benzyl)amino)propyl)carbamate (0.755 g, 100% yield) as a yellow syrup.

Workup

  1. stirringthe reaction mixture stirred at room temperature for 2.5 hours
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution (5 mL)
  3. stirringthe mixture stirred vigorously for 10 minutes
  4. customthen partitioned between ethyl acetate (80 mL) and saturated aqueous ammonium chloride solution (80 mL)
  5. customThe organic phase was separated
  6. washwashed with water (80 mL) and saturated brine (80 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a yellow syrup
  11. customThe product was purified

Sources & evidence

ORD record
ord-ea806387098d49c09067e6f06b8a450d
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

Loading…