Water → Boc-4-aminomethylbicyclo-[2.2.2]octane carboxamide

HRID 365275Notes

Reaction equation

HRID 365275 reaction equation
[C:1]([CH:8]1[CH2:13][C:12]2([CH2:16][NH2:17])[CH2:14][CH2:15][C:9]1([C:18]([OH:20])=O)[CH2:10][CH2:11]2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1C=CN=C1)([N:23]1C=CN=C1)=O.[NH4+].[OH-].O>CN(C=O)C>[C:1]([CH:8]1[CH2:13][C:12]2([CH2:16][NH2:17])[CH2:11][CH2:10][C:9]1([C:18]([NH2:23])=[O:20])[CH2:15][CH2:14]2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 69899061Boc-4-aminomethylbicvclo-[2.2.2]octane carboxylic acid

Product 1

HCID 69901712Boc-4-aminomethylbicyclo-[2.2.2]octane carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution under N2 of 12.0 g (42.5 mmol) of the product from step B in 100 ml of DMF was treated with 8.0 g (49.3 mmol) of carbonyldiimidazole. After 30 min the DMF was evaporated in vacuo to afford 50-60 ml of a light brown paste, which was stirred and treated with 70 ml of conc. NH4OH rapidly added. The initial solution turned to a white paste within 30 min, after which H2O was added up to a total volume of 400 ml to complete precipitation of product, which was triturated and isolated by filtration and washing with H2O, and dried in vacuo to yield the title compound as a white solid.

Workup

  1. customAfter 30 min the DMF was evaporated in vacuo
  2. customto afford 50-60 ml of a light brown paste, which
  3. additionrapidly added
  4. customprecipitation of product, which
  5. customwas triturated
  6. customisolated by filtration
  7. washwashing with H2O
  8. customdried in vacuo

Sources & evidence

ORD record
ord-26b8168ea0c749e5b725d1b973323783
Source dataset
uspto-grants-2000_10
Patent number
US06127333

Reaction notes

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