Benzyl chloroformate → HCID 67357132, compound

HRID 627349Notes

Reaction equation

HRID 627349 reaction equation
[CH2:1]([N:9]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][CH2:17][NH:18][C@@H:11]2[CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(OCC)(=O)C.O>[CH2:25]([O:32][C:33]([N:18]1[C@@H:11]2[CH2:10][N:9]([CH2:1][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][CH2:17]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 11955366(3aR,8aS)-7-Phenethyl-decahydro-pyrrolo[2,3-c]azepine

Product 1

HCID 67357132HCID 67357132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (3aR,8aS)-7-Phenethyl-decahydro-pyrrolo[2,3-c]azepine (4.0 g, 16.37 mmol) (Reference: PCT Int. Appl., 2005097791, 20 Oct. 2005) in ethyl acetate (100 mL) was added a solution of potassium carbonate (6.79 g, 49.1 mmol, 3.0 eq) in water (100 mL). The biphasic solution was cooled to 0° C. then benzylchloroformate (2.80 mL, 19.64 mmol, 1.2 eq) added dropwise. The resulting mixture was stirred for 3 hr at 23° C. The mixture was partitioned and the aqueous layer extracted with Ethyl Acetate. The combined organic layers were washed with water followed by brine and the organic layer dried (Na2SO4), filtered, and the filtrate concentrated to yield an orange oil. The crude was purified using silica gel chromatography (1:2 Ethyl Acetate/Heptane to 100% Ethyl Acetate followed by 12:1 CH2Cl2/Methanol) giving (3aR,8aS)-7-Phenethyl-octahydro-pyrrolo[2,3-c]azepine-1-carboxylic acid benzyl ester.

Workup

  1. customThe mixture was partitioned
  2. extractionthe aqueous layer extracted with Ethyl Acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialthe organic layer dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customto yield an orange oil
  8. customThe crude was purified

Sources & evidence

ORD record
ord-b50e947b76b9473fa63ab52d97fb6307
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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