Benzyl chloroformate → HCID 67357132、化合物

HRID 627349ノート

反応式

HRID 627349 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 67357132HCID 67357132、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b50e947b76b9473fa63ab52d97fb6307
出典データセット
uspto-grants-2016_04
特許番号
US09309252B2

反応ノート

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