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Isopropylamine → Tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate

HRID 426047
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HRID 426047 반응식
C(N)(C)C.[BH4-].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]([OH:28])[CH2:15][CH2:16][N:17]([CH:25]([CH3:27])[CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:12][CH:13]=1.[H-].[Na+].CS(O[CH2:36][CH2:37][CH2:38][O:39][CH3:40])(=O)=O>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]([O:28][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH2:15][CH2:16][N:17]([CH:25]([CH3:26])[CH3:27])[C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH:11]=[CH:12][CH:13]=1
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참가 물질

7

반응물 5

HCID 6363IsopropylamineHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 116939633-Methoxypropyl methanesulfonateHCID 59364370Tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(isopropyl)carbamate

생성물 1

HCID 66704397Tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(isopropyl)carbamate was obtained using procedures analogous to Preparation A, Steps 1-6, using isopropylamine in Step 1 and NaBH4 in Step 6. To a 0° C. solution of tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(isopropyl)carbamate (158 mg, 0.48 mmol) in THF (5 mL) was added NaH (60 mg, 1.45 mmol) and the reaction was allowed to stir for 5 minutes. 3-methoxypropyl methanesulfonate (810 mg, 4.8 mmol) was then added and the reaction was heated to reflux for 2.5 hrs. After cooling to room temperature, the reaction was quenched with saturated ammonium chloride solution at 0° C. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, evaporated and purified via ISCO to afford tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate. MS ESI+ve m/z 422 (M+Na).

후처리

  1. customanalogous to Preparation A, Steps 1-6
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 2.5 hrs
  4. customthe reaction was quenched with saturated ammonium chloride solution at 0° C
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. custompurified via ISCO

출처 및 근거

ORD 기록
ord-0f48f4bf0a2e4170b8ed97fcb960e3b0
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106221B2

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