Hydroxyamine hydrochloride → (S)-5-(((tert-Butyldiphenylsilyl)oxy)methyl)-3-(pyrrolidin-2-yl)isoxazole

HRID 710034ノート

反応式

HRID 710034 の反応式
[Si:1]([O:18][CH2:19][C:20]#[C:21][C:22]([C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1C(OC(C)(C)C)=O)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:37][OH:38].C(=O)(O)[O-].[Na+]>CCO>[Si:1]([O:18][CH2:19][C:20]1[O:38][N:37]=[C:22]([C@@H:24]2[CH2:28][CH2:27][CH2:26][NH:25]2)[CH:21]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 86706745(S)-t-Butyl 2-(4-((tert-butyldiphenylsilyl)oxy)but-2-ynoyl)pyrrolidine-1-carboxylate

生成物 1

HCID 86706746(S)-5-(((tert-Butyldiphenylsilyl)oxy)methyl)-3-(pyrrolidin-2-yl)isoxazole収率 40.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To an EtOH (10 mL) solution of the compound (492 mg) obtained in Example 3-(1), hydroxylamine hydrochloride (139 mg) was added and the mixture was heated under reflux for 17 hours. To the reaction mixture, saturated aqueous sodium bicarbonate (50 ml) was added and the organic layer extracted with AcOEt was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt→MeOH/CHCl3) to give the titled compound (163 mg, brown oil.)

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. extractionthe organic layer extracted with AcOEt
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas further purified by neutral silica gel chromatography (AcOEt→MeOH/CHCl3)

出典と根拠

ORDレコード
ord-eba761ef9d36438fb0106b7e7c3a4a61
出典データセット
uspto-grants-2015_11
特許番号
US09181229B2

反応ノート

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