1-Chloroethyl chloroformate → (3aR,8aS)-Octahydro-pyrrolo[2,3-c]azepine-1-carboxylic acid benzyl ester

HRID 1850554Notes

Reaction equation

HRID 1850554 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]2[CH2:16][N:17](CCC3C=CC=CC=3)[CH2:18][CH2:19][CH2:20][C@@H:14]2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)OC(Cl)C>ClCCCl>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]2[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][C@@H:14]2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 67357132HCID 67357132, compound

Product 1

HCID 67355838(3aR,8aS)-Octahydro-pyrrolo[2,3-c]azepine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (3aR,8aS)-7-Phenethyl-octahydro-pyrrolo[2,3-c]azepine-1-carboxylic acid benzyl ester (1.0 g, 2.64 mmol) in 1,2-dichloroethane (20 mL) was added 1-chloroethyl carbonochloridate (0.286 mL, 2.64 mmol, 1.0 eq) at 0° C. The reaction was stirred with warming to 23° C. over 1 hr, then refluxed for 3 hr. The solvent was removed in vacuo then 20 mL methanol added and the reaction mixture heated to 50° C. for 1 hr. The reaction was concentrated and purified using chromatography (1:2 Ethyl Acetate/Heptane to 100% Ethyl Acetate followed by 12:1 CH2Cl21-Methanol) giving (3aR,8aS)-Octahydro-pyrrolo[2,3-c]azepine-1-carboxylic acid benzyl ester.

Workup

  1. temperaturerefluxed for 3 hr
  2. customThe solvent was removed in vacuo
  3. addition20 mL methanol added
  4. temperaturethe reaction mixture heated to 50° C. for 1 hr
  5. concentrationThe reaction was concentrated
  6. custompurified

Sources & evidence

ORD record
ord-6135ca0a0888455ca9ab3ecf914bb1ea
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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