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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
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HRID 873336 반응식
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
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참가 물질

5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-d6bd65d01e0a4ea3ac7958b5a2f00cf3
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975406B2

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