Benzylamine → N-Benzyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 1444603Notes

Reaction equation

HRID 1444603 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[O:15]1[C:19]2([CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH2:26]([NH:33][CH:22]1[CH2:23][CH2:24][C:19]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:20][CH2:21]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 11791515N-Benzyl-1,4-dioxaspiro[4.5]decan-8-amineYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Na(OAc)3BH 2.03 g (9.6 mmol) was added to a solution of 1,4-dioxa-spiro[4.5]decan-8-one 1.0 g (6.4 mmol) and benzylamine 0.69 g (6.4 mmol) in CH2Cl2 (20 ml) under nitrogen as inert gas and stirring was performed for 2 h at RT. After the addition of CH2Cl2 (80 ml), the organic phase was washed with aqueous saturated NaHCO3 solution. After drying of the separated organic phases over Na2SO4 and filtration, the solvent was removed by distillation and the product benzyl-(1,4-dioxa-spiro[4.5]dec-8-yl)-amine 1.6 g (100% of theoretical) was obtained.

Workup

  1. washthe organic phase was washed with aqueous saturated NaHCO3 solution
  2. dry with materialAfter drying of the separated organic phases over Na2SO4 and filtration
  3. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-513cb42ff2ef4d9f9c6dfa22ec530aaf
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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