5-Aminoisoquinoline → N-(Pyrrolidin-3-yl)isoquinolin-5-amine

HRID 1054022Notes

Reaction equation

HRID 1054022 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.O=[C:13]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O>[NH:15]1[CH2:16][CH2:17][CH:13]([NH:11][C:6]2[C:5]3[CH:4]=[CH:3][N:2]=[CH:1][C:10]=3[CH:9]=[CH:8][CH:7]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 707665-AminoisoquinolineHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57936477N-(Pyrrolidin-3-yl)isoquinolin-5-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a homogenous solution of isoquinolin-5-amine (15 g, 104 mmol) and tert-butyl 3-oxopyrrolidine-1-carboxylate (23.12 g, 125 mmol, 1.2 eq) in AcOH (300 mL) at 0° C. was added dropwise a solution of NaBH(OAc)3 (44.1 g, 208 mmol, 2 eq) in AcOH (200 mL). The mixture was stirred at room temperature overnight and concentrated to dryness. Then, the residue was adjusted to pH 10 by addition of saturated aqueous solution of Na2CO3 and extracted with DCM (×3). The combined organic layers were dried over Na2SO4, filtered and then concentrated under vacuum to afford the expected compound, which was used directly in the next step without further purification.

Workup

  1. concentrationconcentrated to dryness
  2. additionThen, the residue was adjusted to pH 10 by addition of saturated aqueous solution of Na2CO3
  3. extractionextracted with DCM (×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-564021f912804ca09c173e1368a6757f
Source dataset
uspto-grants-2016_07
Patent number
US09394286B2

Reaction notes

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