Hydrochloric Acid → HCID 66823380, compound

HRID 591197Notes

Reaction equation

HRID 591197 reaction equation
[CH2:1]([C:8]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29].Cl>ClCCl>[CH2:31]([O:30][C:28]([N:10]1[CH2:9][C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH2:11]1)=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 10928Ethyl chloroformateHCID 66747306HCID 66747306, compound

Product 1

HCID 66823380HCID 66823380, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled solution of 3-benzyl-3-(3-methoxyphenyl)azetidine (0.45 g, 1.776 mmol) under argon in dichloromethane containing diisopropylamine (0.465 ml, 2.66 mmol) was added dropwise ethyl chloroformate (0.26 ml, 2.7 mmol). The reaction was stirred over night while it was allowed to warm up to room temperature. Hydrochloric acid (1N) was added and the mixture diluted with dichloromethane. The organic layer was separated and the aqueous layer extracted twice with dichloromethane. The combined organic layers were washed subsequently with water, sodium bicarbonate and brine, dried over sodium bicarbonate, filtered and the solvent evaporated to obtain desired product. m=546 mg (61%)

Workup

  1. stirringThe reaction was stirred over night while it
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted twice with dichloromethane
  4. washThe combined organic layers were washed subsequently with water, sodium bicarbonate and brine
  5. dry with materialdried over sodium bicarbonate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-326dfa792863456492f0afdac472ad02
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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