Acetic Acid → Tert-butyl 3-(5-cyanoindolin-1-yl)pyrrolidine-1-carboxylate

HRID 527906ノート

反応式

HRID 527906 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.O=[C:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([CH:17]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16]1)[CH2:2][CH2:3]2)#[N:11]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 219076392,3-Dihydro-1H-indole-5-carbonitrile

生成物 1

HCID 66765193Tert-butyl 3-(5-cyanoindolin-1-yl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of indoline-5-carbonitrile (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-1-carboxylate (166 mg, 0.90 mmol) and HOAc (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2SO4, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

後処理

  1. stirringthe mixture was then stirred at ambient temperature for 2 days
  2. customThe volatiles were removed under vacuum
  3. additionThe residue was diluted with EtOAc
  4. washwashed with 1 N NaOH solution and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-937b76c122d547d294cb695a9b04a76a
出典データセット
uspto-grants-2016_05
特許番号
US09346810B2

反応ノート

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