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

HRID 1372579
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HRID 1372579 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 86632-NaphtholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e1333844a543487dae5349aa1cdaa437
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07157487B2

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