Benzylamine → 3-Benzyl-8-oxa-3-azabicyclo[3.2.1]octane

HRID 1375051Notes

Reaction equation

HRID 1375051 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH2:24][CH:25]1[CH2:29][CH2:28][CH:27]([CH2:30]O)[O:26]1.[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH-].[Na+]>CO>[CH2:32]([N:39]1[CH2:30][CH:27]2[O:26][CH:25]([CH2:29][CH2:28]2)[CH2:24]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 866027052,5-Bis(hydroxymethyl)tetrahydrofuran bis(p-toluenesulfonate)

Product 1

HCID 120692303-Benzyl-8-oxa-3-azabicyclo[3.2.1]octaneYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,5-bis(hydroxymethyl)tetrahydrofuran bis(p-toluenesulfonate) (10 g) and benzylamine (9.7 g) was stirred at 70° C. for 24 hours. To the mixture was added a solution of sodium hydroxide (1.85 g) in methanol (30 ml). After stirring at room temperature for 30 minutes, the mixture was filtered. The filtrate was evaporated, added dichloromethane, and filtered. The filtrate was evaporated under reduced pressure, and purified with column chromatography (silica gel, 250 ml, ethyl acetate:hexane=1:4) to give 3-benzyl-8-oxa-3-azabicyclo[3.2.1]octane (4.05 g) as an oil.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated
  4. additionadded dichloromethane
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. custompurified with column chromatography (silica gel, 250 ml, ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-2a0b9c05e11c4c1f9fedb899130cd66c
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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