Formic Acid → 6,7-dihydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole formic acid salt

HRID 1089033

反応式

HRID 1089033 の反応式
Cl.C[O:3][C:4]1[C:16]2[CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]3[CH2:12][NH:11][CH2:10][C:9]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[O:23]C.B(Br)(Br)Br.CO.[CH:31]([OH:33])=[O:32]>C(Cl)Cl.O>[CH:31]([OH:33])=[O:32].[OH:3][C:4]1[C:16]2[CH2:15][CH:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13]3[CH2:12][NH:11][CH2:10][C:9]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[OH:23]

参加物

7

反応物 4

HCID 284Formic AcidHCID 887MethanolHCID 25134Boron tribromideHCID 199610916,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro 1H-benz[e]isoindole hydrochloride

生成物 1

HCID 199612146,7-dihydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole formic acid salt収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A suspension of 54.5 mg (0.159 mmol) of 6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole hydrochloride, from Step 6, in 2 mL of methylene chloride was cooled to -78° C. and 0.64 mL of a 1M solution of boron tribromide in methylene chloride was added. The reaction mixture was warmed to ambient temperature for 1 h and recooled to 78° C. before 1 mL of methanol was added. After warming to ambient temperature for 1 h, the solvents were removed in vacuo. Additional methanol (5 mL) was added and removed in vacuo. The product was purified on silica gel eluted with 18:1:1 ethyl acetate:formic acid:water to give 29.8 mg (58% yield) of 6,7-dihydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole formic acid salt as an off white powder, m.p. 144° C. MS DCI: M+ 279. 1H NMR (d6 -DMSO) delta 2.95-3.15 (m, 2H), 3.6-3.9 (m, 3H), 4.1-4.3 (m, 2H), 6.43 (d, 1H, J=7.5 Hz), 6.62 (d, 1H, J=7.5 Hz), 7.1-7.3 (m, 5H), 8.3 (s, 1H).

後処理

  1. additionwas added
  2. temperatureAfter warming to ambient temperature for 1 h
  3. customthe solvents were removed in vacuo
  4. additionAdditional methanol (5 mL) was added
  5. customremoved in vacuo
  6. customThe product was purified on silica gel
  7. washeluted with 18:1:1 ethyl acetate

出典と根拠

ORDレコード
ord-f71d2c2cae3b4bf3a05d70f794c425f0
出典データセット
uspto-grants-1990_10
特許番号
US04963568

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