Phthalimide → (S)-tert-butyl (2-(3-chlorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)carbamate

HRID 595803ノート

反応式

HRID 595803 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8](O)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1.[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:23]2[C:19](=[O:29])[C:20]3[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:22]2=[O:24])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 99645701(R)-tert-butyl (2-(3-chlorophenyl)-2-hydroxyethyl)carbamate

生成物 1

HCID 118054581(S)-tert-butyl (2-(3-chlorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)carbamate収率 58.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (R)-tert-butyl (2-(3-chlorophenyl)-2-hydroxyethyl)carbamate (8.12 g, 29.9 mmol) in THF (100 mL) was added phthalimide (6.16 g, 41.8 mmol) and polymer-bound triphenylphosphine (3 mmol of PPh3/1 g of resin, 9.8 g). DTBAD (7.09 g, 30.8 mmol) in THF (20 mL) was added slowly at room temperature to the reaction mixture, which was then stirred at room temperature overnight. The reaction mixture was filtered through Celite and washed with EtOAc. The resulting filtrate was washed with Na2CO3 solution, water and brine, dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo. The crude material was purified by flash chromatography (0-30% EtOAc/heptane) yielding (S)-tert-butyl (2-(3-chlorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)carbamate (58.4%). LCMS (m/z): 301.1 (MH+-Boc), 1.06 min.

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with EtOAc
  3. washThe resulting filtrate was washed with Na2CO3 solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (0-30% EtOAc/heptane)

出典と根拠

ORDレコード
ord-103ed46c889045198061c41e964cc5e9
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

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