Pyrrolidine → HCID 57551761, compound

HRID 907293Notes

Reaction equation

HRID 907293 reaction equation
[CH2:1]([N:8]1[CH:17]=[C:16]([CH:18]=O)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][C:31]=3[CH3:32])[C:23]([NH:25][CH:26]3[CH2:28][CH2:27]3)=[O:24])[CH:14]=2)[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([N:8]1[CH:17]=[C:16]([CH2:18][N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][C:31]=3[CH3:32])[C:23]([NH:25][CH:26]3[CH2:28][CH2:27]3)=[O:24])[CH:14]=2)[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 57551813HCID 57551813, compound

Product 1

HCID 57551761HCID 57551761, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-Benzyl-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-N-cyclopropyl-4-methylbenzamide (0.13 g) was dissolved in dichloromethane (10 mL). Pyrrolidine (0.064 g) was then added and the mixture stirred for 10 minutes before adding sodium triacetoxyborohydride (0.25 g). The mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue purified (SiO2, eluting with 5% methanol in dichloromethane) to give the title compound as a solid (0.038 g).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue purified
  4. wash(SiO2, eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e306088ad3ed4cb6bc63f891b5cd108f
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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