1-Chloroethyl chloroformate → HCID 46196348, compound

HRID 575937Notes

Reaction equation

HRID 575937 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[F:22])([O:13][CH3:14])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[Cl:21][C:17]1[C:16]([F:22])=[C:15]([C:10]2([O:13][CH3:14])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 67402567HCID 67402567, compound

Product 1

HCID 46196348HCID 46196348, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (+)-1-benzyl-3-(3-chloro-2-fluorophenyl)-3-methoxypyrrolidine (1.04 g, 3.25 mmol) in 1,2-dichloroethane (10 ml), was added 1-chloroethyl chloroformate (1.42 ml, 13.08 mmol) and the mixture was heated to reflux for 2 h after which the solvent was evaporated. The mixture was dissolved in methanol (20 ml) and heated to reflux for 1 h, the solvent was evaporated and purified by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50) give the title compound 0.47 g (63%). [a]D=+6.5° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 183-185° C. MS m/z (rel. intensity, 70 eV) 229 (M+, 1), 199 (86), 187 (bp), 157 (49), 133 (42).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h after which the solvent
  3. customwas evaporated
  4. dissolutionThe mixture was dissolved in methanol (20 ml)
  5. temperatureheated
  6. temperatureto reflux for 1 h
  7. customthe solvent was evaporated
  8. custompurified by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50)

Sources & evidence

ORD record
ord-4d9c39296cf04a5e85c433db56848c57
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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