Pyrrolidine → HCID 86654009, compound

HRID 511297Notes

Reaction equation

HRID 511297 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:7]2[C:11]=1[CH2:10][N:9]([CH3:12])[C:8]2=[O:13])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>C1COCC1>[CH3:12][N:9]1[C:8](=[O:13])[C:7]2[C:11](=[C:3]([CH2:1][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:4]=[CH:5][C:6]=2[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86654010HCID 86654010, compound2×

Product 1

HCID 86654009HCID 86654009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-Butyl (7-formyl-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)carbamate (Compound 109C, 23.0 mg, 0.0792 mmol) and sodium triacetoxyborohydride (101 mg, 0.475 mmol) in THF (0.5 mL) was stirred at room temperature for 20 minutes. Pyrrolidine (39.7 uL, 0.475 mmol) was added and the resulting mixture was stirred at room temperature overnight. The THF was removed in vacuo and the crude product was partitioned between EtOAc and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to deliver the desired product. MS (ES+): m/z 346.32 (100) [MH+]; HPLC: tR=0.76 min (UPLC, Analytical).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe THF was removed in vacuo
  3. customthe crude product was partitioned between EtOAc and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c99a21cb77744ca997ade9c01c8bc166
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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