1-Bromo-3-chloropropane → (1S,5R)-3-(3-chloropropyl)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

HRID 12652ノート

反応式

HRID 12652 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.Br[CH2:18][CH2:19][CH2:20][Cl:21]>C1COCC1.CCN(C(C)C)C(C)C.CCOC(C)=O>[Cl:21][CH2:20][CH2:19][CH2:18][N:11]1[CH2:12][C@H:13]2[C@:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=3)([CH2:14]2)[CH2:10]1

参加物

6

反応物 2

HCID 80061-Bromo-3-chloropropaneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

生成物 1

HCID 59337588(1S,5R)-3-(3-chloropropyl)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

To a solution of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (P4, 1.00 g) in dry THF (5 mL), DIPEA (2.4 mL) and 1-bromo-3-chloropropane (3.7 mL) were added and the resulting mixture was heated at reflux for 3 hours. After cooling at room temperature it was diluted with EtOAc (30 mL) washed twice with a saturated solution of NH4Cl in water (20 mL) and once with a saturated aqueous NaHCO3 solution (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with cyclohexane/EtOAc 7:3 to give the title compound as a colourless oil (1.26 g).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. washwashed twice with a saturated solution of NH4Cl in water (20 mL) and once with a saturated aqueous NaHCO3 solution (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with cyclohexane/EtOAc 7:3

出典と根拠

ORDレコード
ord-b5c69ff97ec84d499f849aef7bdff788
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

反応ノート

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