Hydrochloric Acid → (1R)-N-[4-chlorophenyl]-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide

HRID 349785ノート

反応式

HRID 349785 の反応式
[CH3:1][C@:2]12[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[C:5](=[O:12])[CH2:4][C:3]2=[O:13].C(N(CC)CC)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1.Cl>CN(C)C1C=CN=CC=1.ClCCl>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([CH:4]2[C:5](=[O:12])[CH:6]3[C:9]([CH3:10])([CH3:11])[C@@:2]([CH3:1])([CH2:8][CH2:7]3)[C:3]2=[O:13])=[O:30])=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 58805524(1R)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione

生成物 1

HCID 11595173(1R)-N-[4-chlorophenyl]-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To an ice-cooled solution of (1R)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione (0.36 g, 2.0 mmole), triethylamine (0.20 g, 2.0 mmole) and 4-(dimethylamino)pyridine (0.24 g, 2.0 mmole) in dry dichloromethane (25 mL) was added a solution of 4-chlorophenyl isocyanate (0.31 g, 2.0 mmole) in dry dichloromethane (5 mL). The resulting reaction mixture was allowed to stir overnight under a nitrogen atmosphere, during which time it came up to room temperature. It was then stirred at 30° C. for seven hours. The resulting mixture was treated with 2N aqueous HCl (30 mL) and the layers were separated. The aqueous layer was extracted with two additional portions of dichloromethane (50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The desired product was isolated by chromatography on silica gel (10% ethyl acetate/hexane) and recrystallized from 95% ethanol to yield the title compound as a tan solid (0.39 g, 56% yield), mp=88–90° C.; MS (−) ESI m/z=334 (M+H)+; [α]D25=+22.8° (c=1, EtOH).

後処理

  1. customThe resulting reaction mixture
  2. customcame up to room temperature
  3. stirringIt was then stirred at 30° C. for seven hours
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with two additional portions of dichloromethane (50 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-10806a65694949f2a610cffc33edb454
出典データセット
uspto-grants-2007_02
特許番号
US07179943B2

反応ノート

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