Pyrrolidine → N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-pyrrolidineacetamide

HRID 457019Notes

Reaction equation

HRID 457019 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[CH:8][CH:7]=1)=[O:4].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(C(C)C)CC)(C)C>CCOCC.ClCCl.C(OCC)(=O)C>[N:21]1([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([B:12]3[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]3)=[CH:8][CH:7]=2)=[O:4])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 18439275HCID 18439275, compound

Product 1

HCID 18439276N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-pyrrolidineacetamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of intermediate T (0.200 g, 0.677 mmol) in ether (10 mL) was added pyrrolidine (0.241 g, 3.3 mmol), diisopropylethyl amine (0.175 g, 1.3 mmol) and the reaction stirred at room temperature for 48–72 h and monitored by TLC (10% Ethyl acetate: dichloromethane). The reaction was concentrated in vacuo and purified using a 10 g prepacked silica gel column, eluting intermediate U with 10% ethyl acetate:dichloromethane, (0.145 g, 0.439 mmol, 65%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified
  3. washeluting intermediate U with 10% ethyl acetate

Sources & evidence

ORD record
ord-9b08994de8624d5abe941d80e4e83709
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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