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Potassium Carbonate → (R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate

HRID 873336
ノート
印刷プレビュー

反応式

HRID 873336 の反応式
CS([O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.[CH3:18][C:19]1([CH3:33])[C:23]([CH3:25])([CH3:24])[O:22][B:21]([C:26]2[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=2)[O:20]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:24][C:23]1([CH3:25])[C:19]([CH3:18])([CH3:33])[O:20][B:21]([C:26]2[CH:31]=[CH:30][C:29]([O:5][C@@H:6]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]3)=[CH:28][CH:27]=2)[O:22]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

生成物 1

HCID 86710535(R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(S)-tert-Butyl 3-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate (0.53 g, 2.0 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.48 g, 2.2 mmol) and K2CO3 (0.33 g, 2.4 mmol) in DMF (5 mL) were heated at 85° C. for 1 d. The reaction mixture was concentrated in vacuo and Et2O and water were added. The aqueous phase was extracted with Et2O and the combined organics were washed with 1 M NaOH solution (aq), dried (MgSO4), filtered and concentrated in vacuo to give (R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate which was used in the next step without further purification.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo and Et2O and water
  2. additionwere added
  3. extractionThe aqueous phase was extracted with Et2O
  4. washthe combined organics were washed with 1 M NaOH solution (aq)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d6bd65d01e0a4ea3ac7958b5a2f00cf3
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975406B2

反応ノート

読み込み中…

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