Tert-Butylamine → 1-tert-Butyl-3-hydroxyazetidine

HRID 237294Notes

Reaction equation

HRID 237294 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6]([CH:8]1[O:10][CH2:9]1)Cl.C(N(CC)CC)C>C(O)(C)C>[C:1]([N:5]1[CH2:9][CH:8]([OH:10])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 7835EpichlorohydrinHCID 8471Triethylamine

Product 1

HCID 2879861-tert-Butyl-3-hydroxyazetidineYield 85.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butylamine (10 mmol) in isopropylalcohol (20 mL) was added dropwise epichlorohydrine (10 mmol). The mixture was stirred at 25° C. for 16 h. After concentration, the residue was re-dissolved in acetonitrile (20 mL) and triethylamine (20 mmol) was added. The mixture was heated at 100° C. for 24 h, cooled to rt and filtered. The filtrate was concentrated providing 1-tert-butyl-azetidin-3-ol (1.1 g). MS (ESI): mass calcd. for C7H15NO, 129.1; m/z found, 130.1 [M+H]+. 1H NMR (CDCl3): 6.15-5.70 (br s, 1H), 4.84-4.72 (m, 1H), 4.24-4.12 (m, 2H), 4.03-3.87 (m, 2H), 1.37 (s, 9H).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was re-dissolved in acetonitrile (20 mL)
  3. temperatureThe mixture was heated at 100° C. for 24 h
  4. temperaturecooled to rt
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dc15a146c38a427ba4879dbf23510fc1
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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