1,2-Dichloroethane → 3-(Pentylsulfonyl)azetidine hydrochloride
Reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([S:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])=[O:13])[CH2:9]2)C=CC=CC=1.[Cl:26]CCCl.ClC(OC(Cl)C)=O>CO>[ClH:26].[CH2:15]([S:12]([CH:10]1[CH2:11][NH:8][CH2:9]1)(=[O:14])=[O:13])[CH2:16][CH2:17][CH2:18][CH3:19]Participants
Conditions
- Temperature
- 70 °C
Procedure
A 16 mL flask was charged with 1-(diphenylmethyl)-3-(pentylsulfonyl)azetidine (136 mg, 0.38 mmol; which may be prepared as described in Step 3) and 1,2-dichloroethane (1.7 mL). 1-Chloroethyl chloroformate (53 μL, 0.49 mmol) was added and the reaction mixture was stirred at 70° C. for 1.5 h. After cooling to room temperature, methanol (1.7 mL) was added and the reaction mixture stirred at 70° C. for 1.5 h. The reaction mixture was concentrated dryness. LCMS analysis showed a mixture of the final product and the starting material. The residue was dissolved again in 1,2-dichloroethane and 1-chloroethyl chloroformate (4 eq., 164 μL) was added. The reaction mixture was stirred at 70° C. for 5 h and overnight after addition of methanol. No starting material was detected by TLC monitoring, so the reaction mixture was concentrated to dryness and the resulting solid triturated in pentane to give the title product (39 mg, 45%) as a dark orange oil.
Workup
- temperatureAfter cooling to room temperature
- stirringthe reaction mixture stirred at 70° C. for 1.5 h
- concentrationThe reaction mixture was concentrated dryness
- additiona mixture of the final product
- dissolutionThe residue was dissolved again in 1,2-dichloroethane
- stirringThe reaction mixture was stirred at 70° C. for 5 h and overnight
- concentrationwas concentrated to dryness
- customthe resulting solid triturated in pentane
Sources & evidence
- ORD record
- ord-19ad69a90c1941418257522ddf920f35
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051321B2
Reaction notes
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