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

HRID 456258
ノート
印刷プレビュー

反応式

HRID 456258 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-febe6d192b034b3a913f539bb79d281d
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08497383B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート