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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
ノート
印刷プレビュー

反応式

HRID 537256 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1125ef8162c84c72957e49a467001e22
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859774B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート