Sodium Iodide → HCID 89514376, compound

HRID 1778573Notes

Reaction equation

HRID 1778573 reaction equation
[C:1]([NH:4][C:5]([CH2:26][CH2:27][CH2:28]Cl)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[Na+].[I-].[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>C(#N)C.O>[C:1]([NH:4][C:5]([CH2:26][CH2:27][CH2:28][N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 31268PyrrolidineHCID 89515406HCID 89515406, compound

Product 1

HCID 89514376HCID 89514376, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-acetamido-N-tert-butyl-2-(3-chloropropyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (0.39 g, 0.9 mmol) in acetonitrile was treated with NaI (10% mol) and pyrolidine (0.75 mL, 9 mmol). The mixture was warmed to 50° C. and stirred overnight. After cooling to room temperature, the reaction was diluted with water, extracted with dichloromethane, dried over MgSO4, and concentrated to give crude 2-acetamido-N-tert-butyl-2-(3-(pyrrolidin-1-yl)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (0.31 g). This material was used in the next step without further purification. ESI MS found for C25H48BN3O4 m/z [466.6 (M+1)].

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-939b1ccc95384e41a726ff1242342fce
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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