Water → (E,1R,3aR,7aS)-4-(bromomethylene)-octahydro-1-{(R)-1-hydroxyethyl}-7a-methyl-1H-indene-1-ol

HRID 1922636ノート

反応式

HRID 1922636 の反応式
[Br:1]/[CH:2]=[C:3]1/[C@H:4]2[C@:8]([CH3:12])([CH2:9][CH2:10][CH2:11]/1)/[C:7](=[CH:13]/[CH3:14])/[CH2:6][CH2:5]2.CS(N)(=O)=[O:17].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+].[OH2:84]>C(OCC)(=O)C.C(O)(C)(C)C>[Br:1]/[CH:2]=[C:3]1/[C@H:4]2[C@:8]([CH3:12])([CH2:9][CH2:10][CH2:11]/1)[C@:7]([C@H:13]([OH:17])[CH3:14])([OH:84])[CH2:6][CH2:5]2

参加物

8

反応物 5

HCID 962Water2 回HCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 59456521(1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene2 回

生成物 1

HCID 59456516(E,1R,3aR,7aS)-4-(bromomethylene)-octahydro-1-{(R)-1-hydroxyethyl}-7a-methyl-1H-indene-1-ol収率 85.3%

試薬・触媒・溶媒 2

HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of (1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene (Compound 21: 19.2 mg, 0.07524 mmol), methanesulfonamide (21.5 mg, 0.2257 mmol) and AD-mix-α (105 mg), t-butanol (0.4 ml) and water (0.4 ml) were added, and the reaction mixture was stirred at room temperature for 48 hours. Sodium sulfite (113 mg) was added thereto and the resulting mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added thereto, and the resulting mixture was extracted 3 times with ethyl acetate. The organic layer was washed with 2 M aqueous potassium hydroxide solution (1 ml) and saturated brine (2.5 ml), and dried over sodium sulfate, followed by evaporation under reduced pressure. The obtained crude product (23.2 mg) was purified by flash column chromatography to obtain (E,1R,3aR,7aS)-4-(bromomethylene)-octahydro-1-{(R)-1-hydroxyethyl}-7a-methyl-1H-indene-1-ol (18.6 mg, 85.3%).

後処理

  1. additionwere added
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. extractionthe resulting mixture was extracted 3 times with ethyl acetate
  4. washThe organic layer was washed with 2 M aqueous potassium hydroxide solution (1 ml) and saturated brine (2.5 ml)
  5. dry with materialdried over sodium sulfate
  6. customfollowed by evaporation under reduced pressure
  7. customThe obtained crude product (23.2 mg)
  8. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-fbc14994483648fc8efe3fd339f15b47
出典データセット
uspto-grants-2012_05
特許番号
US08173824B2

反応ノート

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