3-Benzyloxy-1-(tert.butyl)azetidine → 1-tert-Butyl-3-hydroxyazetidine

HRID 328903Notes

Reaction equation

HRID 328903 reaction equation
C([O:8][CH:9]1[CH2:12][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:10]1)C1C=CC=CC=1>[Ni].C(O)C>[C:13]([N:11]1[CH2:12][CH:9]([OH:8])[CH2:10]1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 1

HCID 205173323-Benzyloxy-1-(tert.butyl)azetidine

Product 1

HCID 2879861-tert-Butyl-3-hydroxyazetidineYield 76%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4.4 parts of 3-benzyloxy-1-(tert.butyl)azetidine in 30 parts of ethanol was taken into an autoclave together with 2 parts of Raney nickel as catalyst. Under a hydrogen gas pressure of 100 atmospheres, the mixture was stirred at 40° C. for 15 hours to perform the reduction. The catalyst was separated by filtration, and the remaining ethanol solution was concentrated to dryness. The resulting oily substance was dissolved in n-hexane and cooled. As a result 2.0 parts of 1-(tert.-butyl)-3-azetidinol melting at 42° - 43° C. The yield was 76%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the product are as follows:

Workup

  1. customThe catalyst was separated by filtration
  2. concentrationthe remaining ethanol solution was concentrated to dryness
  3. dissolutionThe resulting oily substance was dissolved in n-hexane
  4. temperaturecooled

Sources & evidence

ORD record
ord-db82225784564761821714242e8703a7
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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