Sodium borohydride → (3-(4-(4-Chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol

HRID 1506378ノート

反応式

HRID 1506378 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]3[O:18][N:17]=[C:16]4[C:19]5[C:24]([CH2:25][CH2:26][C:15]=34)=[CH:23][C:22]([CH:27]([OH:30])CO)=[CH:21][CH:20]=5)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+].[BH4-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]3[O:18][N:17]=[C:16]4[C:19]5[C:24]([CH2:25][CH2:26][C:15]=34)=[CH:23][C:22]([CH2:27][OH:30])=[CH:21][CH:20]=5)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 671720721-(3-(4-(4-Chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol

生成物 1

HCID 67168754(3-(4-(4-Chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of 1-(3-(4-(4-chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol (Preparation 27C, 0.05 g, 0.118 mmol) in methanol (1.0 mL) at 0° C. was added a solution of sodium periodate (0.030 g, 0.142 mmol) in water (1.0 mL) dropwise. The white heterogeneous reaction mixture was stirred for 40 mins. at the same temperature and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhyd. sodium sulfate and concentrated. The residue was taken in methanol (2 mL) and treated with sodium borohydride (5.35 mg, 0.142 mmol) at room temperature. After 1 h, the reaction was quenched with saturated. aq. sodium bicarbonate. After stirring for 30 min, the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried over anhyd. magnesium sulfate and concentrated to yield (3-(4-(4-chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol.

後処理

  1. customThe white heterogeneous reaction mixture
  2. customat the same temperature and then partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried over anhyd
  5. concentrationsodium sulfate and concentrated
  6. waitAfter 1 h
  7. customthe reaction was quenched with saturated
  8. stirringAfter stirring for 30 min
  9. customthe reaction mixture was partitioned between ethyl acetate and water
  10. washThe ethyl acetate layer was washed with brine
  11. customdried over anhyd
  12. concentrationmagnesium sulfate and concentrated

出典と根拠

ORDレコード
ord-791adea887e040d690e54bd889b7c506
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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