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Hydrochloric Acid → (R,Z)-2-tert-butyl 8a-methyl 7-(hydroxymethylene)-6-oxo-3,4,6,7,8,8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate

HRID 537256
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HRID 537256 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[O:11]=[C:12]1[CH2:21][CH2:20][C@@:19]2([C:22]([O:24][CH3:25])=[O:23])[C:14]([CH2:15][CH2:16][N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:18]2)=[CH:13]1.[CH:33](OCC(F)(F)F)=[O:34].Cl>CCOCC.C(OCC)(=O)C.O>[OH:34]/[CH:33]=[C:21]1\[C:12](=[O:11])[CH:13]=[C:14]2[C@:19]([C:22]([O:24][CH3:25])=[O:23])([CH2:20]\1)[CH2:18][N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:16][CH2:15]2
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 1416812,2,2-Trifluoroethyl formateHCID 2733832Lithium hexamethyldisilazaneHCID 109468002-tert-butyl 8a-methyl (8aR)-6-oxo-1,2,3,4,6,7,8,8a-octahydroisoquinoline-2,8a-dicarboxylate

생성물 1

HCID 58333286(R,Z)-2-tert-butyl 8a-methyl 7-(hydroxymethylene)-6-oxo-3,4,6,7,8,8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate수율 100%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

Lithium hexamethyldisilazide (12.93 ml, 12.93 mmol) was added to diethyl ether (20 mL) at −78° C. (R)-2-tert-butyl 8a-methyl 6-oxo-3,4,6,7,8,8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate (WO2005087769) (1.0 g, 3.23 mmol) in ether (5 mL) was added followed by the addition of 2,2,2-trifluoroethyl formate (2.51 ml, 25.9 mmol) after 20 minutes. The reaction was stirred at −78° C. for 2 hours then allowed to slowly warm to room temperature. 1M hydrochloric acid (8 mL) was added, followed by water (10 mL) and ethyl acetate (10 mL). The organic phase was separated, washed with brine, dried (magnesium sulfate) and solvent removed to give (R,Z)-2-tert-butyl 8a-methyl 7-(hydroxymethylene)-6-oxo-3,4,6,7,8,8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate (1.09 g) as a yellow oil. LCMS (Method F, ES-API): RT 1.99 min, m−H=336.

후처리

  1. additionwas added
  2. temperatureto slowly warm to room temperature
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (magnesium sulfate) and solvent
  6. customremoved

출처 및 근거

ORD 기록
ord-1125ef8162c84c72957e49a467001e22
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859774B2

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