Methanol → 3-(3-Methoxypropoxy)azetidine hydrochloride
Reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClCCCl>[ClH:1].[CH3:30][O:29][CH2:28][CH2:27][CH2:26][O:25][CH:23]1[CH2:24][NH:21][CH2:22]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
1-Chloroethyl chloroformate (210 μL, 1.9 mmol) was added to a solution of 1-benzhydryl-3-(3-methoxypropoxy)-azetidine (460 mg, 1.5 mmol) in 1,2-dichloroethane (7 mL) at room temperature. The reaction mixture was then heated up to 70° C. and stirred for 1.5 hours. After cooling down to room temperature, methanol (7 mL) was added and the mixture was again warmup up to 70° C. and stirred for an additional 2 hours. After concentration to dryness, the crude was triturated in pentane (2×10 mL) to afford a yellow oil (247 mg, 92%) which was used in the next step without further purification.
Workup
- temperatureAfter cooling down to room temperature
- customwas again warmup up to 70° C.
- stirringstirred for an additional 2 hours
- concentrationAfter concentration to dryness
- customthe crude was triturated in pentane (2×10 mL)
Sources & evidence
- ORD record
- ord-ef19c6995807484b83c6ea2d92e4a218
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846711B2
Reaction notes
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