1-Chloroethyl chloroformate → HCID 69068456, compound

HRID 1045705Notes

Reaction equation

HRID 1045705 reaction equation
C1([C@H]([N:9]2[C@H:17]3[C@@H:13]([CH2:14][O:15][CH2:16]3)[O:12][CH2:11][CH2:10]2)C)C=CC=CC=1.[Cl:18]C(OC(Cl)C)=O>ClCCCl>[ClH:18].[CH2:16]1[C@@H:17]2[C@H:13]([O:12][CH2:11][CH2:10][NH:9]2)[CH2:14][O:15]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 57870183HCID 57870183, compound

Product 1

HCID 69068456HCID 69068456, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (3aS,7aR)-7-((1R)-1-phenyl-ethyl)-hexahydro-2,4-dioxa-7-aza-indene (1.0 g, 4.9 mmol) and 1-chloroethyl chloroformate (2.7 ml, 25 mmol) in 1,2-dichloroethane (15 mL) was refluxed for 15 hours and cooled to room temperature. After the reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved into methanol and the mixture was refluxed for 2 hours. The reaction mixture was cooled to room temperature and concentrated. Ethyl acetate was added to the residue and the precipitated white solid of (3aS,7aR)-hexahydro-2,4-dioxa-7-aza-indene hydrochloride was triturated and collected by filtration (0.74 g, 4.5 mmol, 91%).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved into methanol
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated
  6. additionEthyl acetate was added to the residue
  7. customthe precipitated white solid of (3aS,7aR)-hexahydro-2,4-dioxa-7-aza-indene hydrochloride was triturated
  8. filtrationcollected by filtration (0.74 g, 4.5 mmol, 91%)

Sources & evidence

ORD record
ord-36fc1f1463ec47aaa1b69bcb1d72cb30
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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