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Sodium cyanoborohydride → Methyl 3-[N-(p-Chlorobenzyl)-3-benzyl-5-(benzoyloxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 327229
ノート
印刷プレビュー

反応式

HRID 327229 の反応式
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:14]=3)[C:9]([C:25](=O)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37][CH3:38])=[O:36])=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>ClC(Cl)C.[Zn+2].[I-].[I-]>[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:14]=3)[C:9]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37][CH3:38])=[O:36])=[CH:4][CH:3]=1
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

5

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 18947606Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-benzoyloxyindol-2-yl]-2,2-dimethylpropanoate

生成物 1

HCID 18947558Methyl 3-[N-(p-Chlorobenzyl)-3-benzyl-5-(benzoyloxy)indol-2-yl]-2,2-dimethylpropanoate

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
65 °C

実験手順

Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-(benzoyloxy)indol-2-yl]-2,2-dimethylpropanoate (360 mg) (prepared in Step A of Example 9), 800 mg of ZnI2, and 500 mg of sodium cyanoborohydride were stirred in 5 mL of dichloroethane at RT under argon for 30 min. The temperature was then raised to 65° C. for 3 hr. After the solution had cooled, it was poured onto 10 mL of NH4OAc (25% solution), extracted with 3×15 mL of ether, washed with 10 mL of H2O and dried (MgSO4). The solution was evaporated to dryness and the residue was chromatographed on silica gel to yield the title compound as a white foam.

後処理

  1. temperatureAfter the solution had cooled
  2. extractionextracted with 3×15 mL of ether
  3. washwashed with 10 mL of H2O
  4. dry with materialdried (MgSO4)
  5. customThe solution was evaporated to dryness
  6. customthe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-930a0d5ed0e54fe38ef5fccc656a694f
出典データセット
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05272145

反応ノート

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