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Benzyl Alcohol → 1-Tert-butyl 3-ethyl (3R,4S)-4-{[(benzyloxy)carbonyl]amino}pyrrolidine-1,3-dicarboxylate

HRID 456258
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인쇄 미리보기

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HRID 456258 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.CC[N:48]([CH:52](C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:10]([NH:48][C:52](=[O:36])[O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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6

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HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11437663rac-(3R,4R)-1-[(tert-butoxy)carbonyl]-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid

생성물 1

HCID 701984471-Tert-butyl 3-ethyl (3R,4S)-4-{[(benzyloxy)carbonyl]amino}pyrrolidine-1,3-dicarboxylate

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
80 °C

실험 절차

A mixture of (3S*,4S*)-1-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid (see Example 12, Step 2) (7.01 g, 24.4 mmol), benzyl alcohol (3.16 g, 29.15 mmol), diphenylphosphoryl azide (8.06 g, 29.3 mmol) and DIPEA (3.76 g, 29.15 mmol) in toluene (320 mL) was stirred at 80° C. for 15 hours. The toluene was partially evaporated, water was added and the mixture was extracted with CHCl3. The combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 5→15% MeOH in CHCl3 giving the title product.

후처리

  1. customThe toluene was partially evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted with CHCl3
  4. dry with materialThe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 5→15% MeOH in CHCl3 giving the title product

출처 및 근거

ORD 기록
ord-febe6d192b034b3a913f539bb79d281d
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497383B2

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