Sodium Iodide → Di-tert-butyl 8-(4-methoxyphenyl)-9-oxo-5-propoxy-1,2,3,9-tetrahydro-6-aza-cyclopenta[a]naphthalen-6-ylmethyl phosphate

HRID 2047981노트

반응식

HRID 2047981 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[C:13]([O:23][CH2:24][CH2:25][CH3:26])[CH:14]=[C:15]4[CH2:22][CH2:21][CH2:20][C:16]4=3)[NH:11][CH:10]=2)=[CH:5][CH:4]=1.[I-].[Na+].[H-].[Na+].[P:31]([O:43][CH2:44]Cl)([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CN(C=O)C>[P:31]([O:43][CH2:44][N:11]1[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:18](=[O:19])[C:17]2[C:12]1=[C:13]([O:23][CH2:24][CH2:25][CH3:26])[CH:14]=[C:15]1[CH2:22][CH2:21][CH2:20][C:16]1=2)([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:32]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 11701630Di-tert-butyl (chloromethyl) phosphateHCID 584925468-(4-Methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

생성물 1

HCID 46224418Di-tert-butyl 8-(4-methoxyphenyl)-9-oxo-5-propoxy-1,2,3,9-tetrahydro-6-aza-cyclopenta[a]naphthalen-6-ylmethyl phosphate수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a DMF solution (10 ml) of 8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (400 mg, 1.15 mmol) and sodium iodide (343 mg, 2.29 mmol) was added sodium hydride (60% oil base, 74.9 mg, 1.72 mmol), and the mixture was then stirred for 10 minutes at room temperature. To the resulting mixture was added a DMF solution (20 ml) of di-tert-butyl chloromethyl phosphate (888 mg, 3.43 mmol), and the mixture was then stirred at 40° C. for 4 hours. The reaction mixture was ice-cooled, ice water was added thereto, and then the reaction mixture was subjected to extraction using ethyl acetate. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified using medium pressure liquid chromatography (NH silica gel, n-hexane:ethyl acetate=100:0→0:100). The purified product was concentrated under reduced pressure, giving a white powder of di-tert-butyl 8-(4-methoxyphenyl)-9-oxo-5-propoxy-1,2,3,9-tetrahydro-6-aza-cyclopenta[a]naphthalen-6-ylmethyl phosphate (263 mg, yield: 40%).

후처리

  1. stirringthe mixture was then stirred at 40° C. for 4 hours
  2. temperaturecooled
  3. extractionthe reaction mixture was subjected to extraction
  4. washThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified
  8. concentrationThe purified product was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2db4df497d8746aa8176b3e07b4c4d17
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592593B2

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