Nitrogen → N-tert-butoxycarbonyl-4-(pyrrolidin-1-yl)pentan-1-amine

HRID 1044810Notes

Reaction equation

HRID 1044810 reaction equation
N#N.[NH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.O=[C:9]([CH3:21])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CC#N>[C:16]([O:15][C:14]([NH:13][CH2:12][CH2:11][CH2:10][CH:9]([N:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:21])=[O:20])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 5

HCID 947NitrogenHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21478928tert-Butyl (4-oxopentyl)carbamate

Product 1

HCID 67496233N-tert-butoxycarbonyl-4-(pyrrolidin-1-yl)pentan-1-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of pyrrolidine (79 mg, 1.11 mmol) in dry CH3CN (6 mL) was added tert-butyl (4-oxopentyl)carbamate (291 mg, 1.44 mmol) followed by Na(OAc)3BH (680 mg, 2.88 mmol) at rt. The reaction mixture was stirred at rt until completion of the reaction. Sat. aq. NaHCO3 was then added and the mixture extracted with EA (3×). The combined org. extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by FC(CH2Cl2-MeOH—NH3) to give pure N-tert-butoxycarbonyl-4-(pyrrolidin-1-yl)pentan-1-amine as a colorless oil. LC-MS-conditions 05c: tR=0.53 min; [M+H]+=257.41. The title compound was obtained after Boc deprotection using 4N HCl in dioxane (10.0 eq.) in CH2Cl2 at rt as a colorless oil.

Workup

  1. extractionthe mixture extracted with EA (3×)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by FC(CH2Cl2-MeOH—NH3)

Sources & evidence

ORD record
ord-58a8d22ccbb0416589b584b06287807d
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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