Methanol → (+/-)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS,5RS)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamide

HRID 220103ノート

反応式

HRID 220103 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[C:9]([NH:11][CH:12]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:17][CH:16]3[CH:14]([O:15]3)[CH2:13]2)=[O:10])[CH2:3][CH2:2]1.[BH4-].[Na+].CO.O>C(O)(C)(C)C.C(OCC)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:35][CH2:36]2)[C:9]([NH:11][CH:12]2[CH2:13][CH:14]([OH:15])[CH2:16][CH2:17][CH:18]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)=[O:10])[CH2:2][CH2:3]1

参加物

7

反応物 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86601279(+/-)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide2 回

生成物 1

HCID 68986614(+/-)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS,5RS)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamide収率 68.2%

試薬・触媒・溶媒 2

HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

16.5 g of (±)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide (compound E1) are dissolved in 500 ml of tert-butanol, 5.0 g of sodium borohydride are added and the reaction mixture is heated to boiling. After slow addition of 70 ml of methanol, the reaction mixture is cooled and treated with 200 ml of water and 150 ml of ethyl acetate. The organic phase is dried using sodium sulfate, concentrated and the residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate in the ratio 1/2. 11.3 g of the title compound are obtained.

後処理

  1. temperaturethe reaction mixture is heated to boiling
  2. temperaturethe reaction mixture is cooled
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customthe residue is chromatographed on silica gel using
  6. additiona mixture of petroleum ether/ethyl acetate in the ratio 1/2

出典と根拠

ORDレコード
ord-e17d2cb1e00f4610a2505c89e51744cc
出典データセット
uspto-grants-2012_06
特許番号
US08202880B2

反応ノート

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