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Chlorosuccinimide → (S)-tert-Butyl 2-(5-((pyridin-3-yloxy)methyl)isoxazol-3-yl)pyrrolidine-1-carboxylate

HRID 710031
ノート
印刷プレビュー

反応式

HRID 710031 の反応式
[OH:1][N:2]=[CH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1C(=O)N(Cl)C(=O)C1.[CH2:24]([O:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[C:25]#[CH:26].C(=O)(O)[O-].[Na+]>C1COCC1.CCN(CC)CC.CN(C=O)C>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([O:27][CH2:24][C:25]2[O:1][N:2]=[C:3]([C@@H:4]3[CH2:8][CH2:7][CH2:6][N:5]3[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:26]=2)[CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 114236223-(Prop-2-ynyloxy)pyridineHCID 86706742(S)-t-Butyl 2-((hydroxyimino)methyl)pyrrolidine-1-carboxylate

生成物 1

HCID 86706743(S)-tert-Butyl 2-(5-((pyridin-3-yloxy)methyl)isoxazol-3-yl)pyrrolidine-1-carboxylate収率 55.2%

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
溶媒
HCID 8028Tetrahydrofuran溶媒2 回
HCID 8471Triethylamine溶媒

実験手順

To a DMF (60 mL) solution of the compound (8.57 g) obtained in Example 2-(1), NCS (5.341 g) was added in small portions at 0° C. and the mixture was stirred at room temperature for an hour. The reaction mixture was cooled to 0° C. and after adding a solution of 3-(prop-2-yn-1-yloxy)pyridine (2.663 g) in THF (5 mL) and a solution of Et3N (5.6 mL) in THF (15 mL), the resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was added to saturated aqueous sodium bicarbonate (200 mL), followed by extraction with AcOEt (200 mL). The resulting organic layer was washed with brine (200 mL), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (3.81 g, pale yellow solid.)

後処理

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionfollowed by extraction with AcOEt (200 mL)
  3. washThe resulting organic layer was washed with brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-eb8e1c3588984a42b6af5122cccf4046
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181229B2

反応ノート

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