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

HRID 527906노트

반응식

HRID 527906 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-937b76c122d547d294cb695a9b04a76a
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346810B2

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