Water → HCID 123959447, compound

HRID 2205080Notes

Reaction equation

HRID 2205080 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[O:3]1.C([O-])(=O)C.[NH4+].I([O-])(=O)(=O)=O.[Na+].O>CC(C)=O.C1(C)C=CC=CC=1>[C:22]([O:21][C:20]([NH:19][C:15]1([C:12]2[CH:11]=[CH:10][C:9]([B:4]([OH:5])[OH:3])=[CH:14][CH:13]=2)[CH2:18][CH2:17][CH2:16]1)=[O:26])([CH3:25])([CH3:23])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 58326444tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 123959447HCID 123959447, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutyl}carbamate [Int-1B] (5.63 g, 20.0 mmol, 1 eq) in 191 mL acetone is added ammonium acetate (7.38 g, 95.6 mmol, 4.78 eq). After the addition of sodium periodate (13.6 g, 63.6 mmol, 3.15 eq) the reaction mixture was stirred overnight at rt. Then, the white suspension was treated with water. The remaining solid was isolated by filtration and treated with toluene that was directly removed by a rotary evaporator. This procedure was repeated three times. The remaining solid was dried in vacuo at 60° C. overnight to give 3.87 g (75%) of the title compound in 85% purity (UPLC, area-%).

Workup

  1. customThe remaining solid was isolated by filtration
  2. customwas directly removed by a rotary evaporator
  3. customThe remaining solid was dried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-bb016a4a605f476c97c4a0992c23cad0
Source dataset
uspto-grants-2016_06
Patent number
US09370517B2

Reaction notes

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