Methanol → Benzyl{(2R,3S)-3-hydroxy-4-[(tripropan-2-ylsilyl)oxy]butan-2-yl}carbamate

HRID 909584ノート

反応式

HRID 909584 の反応式
[N+](C1C=CC(C([O:10][C@H:11]([CH2:25][O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[C@@H:12]([CH3:24])[NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=O)=CC=1)([O-])=O.[H-].C([Al+]CC(C)C)C(C)C.CO.[OH-].[Na+]>C(Cl)Cl>[OH:10][C@H:11]([CH2:25][O:26][Si:27]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:34]([CH3:35])[CH3:36])[C@H:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:24]

参加物

6

反応物 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 66682207(5R,6S)-5,10-Dimethyl-3-oxo-1-phenyl-9,9-di(propan-2-yl)-2,8-dioxa-4-aza-9-silaundecan-6-yl 4-nitrobenzoate

生成物 1

HCID 86649570Benzyl{(2R,3S)-3-hydroxy-4-[(tripropan-2-ylsilyl)oxy]butan-2-yl}carbamate収率 65%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-40 °C

実験手順

(5R,6S)-5,10-Dimethyl-3-oxo-1-phenyl-9,9-di(propan-2-yl)-2,8-dioxa-4-aza-9-silaundecan-6-yl 4-nitrobenzoate (7.90 g, 14.5 mmol) synthesized in Example (89c) was dissolved in methylene chloride (150 mL), and diisobutylaluminum hydride (1.0 mol/L hexane solution, 30.0 mL, 30.0 mmol) was added, followed by stirring at −40° C. for 8 hours under nitrogen atmosphere. The reaction solution was brought back to 0° C., and methanol (5.0 mL) was added, followed by addition of a 5N aqueous sodium hydroxide solution (150 mL), and extraction was carried out with methylene chloride (200 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-15%) to afford the desired compound (3.70 g, yield 65%) as a colorless liquid.

後処理

  1. customwas brought back to 0° C.
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-15%)

出典と根拠

ORDレコード
ord-5e86b0d72fa64d61964e0a312fc01293
出典データセット
uspto-grants-2011_09
特許番号
US08017610B2

反応ノート

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