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

HRID 527906Notes

Reaction equation

HRID 527906 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-937b76c122d547d294cb695a9b04a76a
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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