Sodium Iodide → 3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol

HRID 19668

反応式

HRID 19668 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.C(N(CC)CC)C.Br[CH2:25][CH2:26][CH2:27][OH:28].[Na+].[I-]>O1CCCC1.C(OCC)(=O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][N:11]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:10]3)=[CH:7][CH:8]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 123083-Bromo-1-propanolHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

生成物 1

HCID 593375943-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (151 mg, prepared following the procedure reported in WO 2005080382) in dry tetrahydrofuran (3.3 mL), triethylamine (0.112 mL), 3-bromo-1-propanol (0.073 mL) and NaI were added and the resulting mixture was heated at reflux for 4 hours. After cooling at room temperature it was diluted with ethyl acetate (20 mL), washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (10 g) eluting with dichloromethane/methanol from 99/1 to 97/3 to give the title compound as a colourless oil (144 mg).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. washwashed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by a silica SPE cartridge (10 g)
  7. washeluting with dichloromethane/methanol from 99/1 to 97/3

出典と根拠

ORDレコード
ord-7355567d588f487aa754fd38b156d94d
出典データセット
uspto-grants-2010_06
特許番号
US07745458B2

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