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2-Naphthol → (2S,4S)-1-tert-Butyl 2-methyl 4-(naphthalen-2-yloxy)pyrrolidine-1,2-dicarboxylate

HRID 1372579
ノート
印刷プレビュー

反応式

HRID 1372579 の反応式
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([OH:27])[CH2:24][C@H:23]1[C:28]([O:30][CH3:31])=[O:29])=[O:21])([CH3:18])([CH3:17])[CH3:16].[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([O:27][C:34]2[CH:33]=[CH:32][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=2)[CH2:24][C@H:23]1[C:28]([O:30][CH3:31])=[O:29])=[O:21])([CH3:18])([CH3:17])[CH3:16]
参加物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 86632-NaphtholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

生成物 1

HCID 67406330(2S,4S)-1-tert-Butyl 2-methyl 4-(naphthalen-2-yloxy)pyrrolidine-1,2-dicarboxylate収率 84.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

DIAD (3.72 ml, 18.9 mmol) was added to a solution of methyl (2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarboxylate (4.22 g, 17.2 mmol), 2-naphthol (2.73 g, 18.9 mmol) and triphenylphosphine (4.96 g, 18.9 mmol) in THF (80 ml) under stirring at room temperature in a nitrogen gas stream. The mixture was stirred overnight at room temperature. The residue, which had been obtained by concentrating the reaction mixture under reduced pressure, was purified by chromatography on a silica gel column (silica gel: 600 g), whereby from chloroform/ethyl acetate (10/1) eluate fractions, the title compound (5.37 g) was obtained as an amorphous substance (this compound was provided for the subsequent reaction without further purification).

後処理

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe residue, which had been obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure
  4. customwas purified by chromatography on a silica gel column (silica gel: 600 g), whereby from chloroform/ethyl acetate (10/1) eluate fractions

出典と根拠

ORDレコード
ord-e1333844a543487dae5349aa1cdaa437
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07157487B2

反応ノート

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