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Formic Acid → (3aRS,4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

HRID 2293300
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HRID 2293300 반응식
[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]2[CH:10]([C:11]([CH3:26])([CH3:25])[NH:12][CH:13]2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28](O)=O.C=O>[OH-].[Na+]>[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]2[CH:10]([C:11]([CH3:25])([CH3:26])[N:12]([CH3:28])[CH:13]2[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=2)[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 69952519(3aRS,4RS,6aSR)-2-benzyl-4-(4-bromo-benzyl)-6,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

생성물 1

HCID 69953772(3aRS,4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione수율 85.9%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide
용매

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온도
100 °C

실험 절차

A mixture of 3.88 g (9.1 mmol) of (3aRS,4RS,6aSR)-2-benzyl-4-(4-bromo-benzyl)-6,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione, 85% formic acid (4.9 g, 90 mmol) and 35% formalin solution (2.6 g, 30 mmol) were heated to 100° C. for 5.5 hours. After cooling 1N NaOH (50 ml) was added and the mixture was extracted four times with dichloromethane. The organic phase was concentrated and the residue was separated chromatographically (hexane/ethyl acetate 3:1+1% triethylamine). 3.45 g of (3aRS, 4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione were isolated as a yellowish oil. FAB-MS: 441 ([M+H]+, 40); 271 (100); 212 (5); 169 (11); 136 (14); 110 (26); 91 (42).

후처리

  1. additionwas added
  2. extractionthe mixture was extracted four times with dichloromethane
  3. concentrationThe organic phase was concentrated
  4. customthe residue was separated chromatographically (hexane/ethyl acetate 3:1+1% triethylamine)

출처 및 근거

ORD 기록
ord-e5a788c2b1f14804b0e297c5aa895b7e
출처 데이터셋
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05686459

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