Azepane → HCID 20992498, compound

HRID 404659Notes

Reaction equation

HRID 404659 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.O.O=[CH:19][C:20]([OH:22])=[O:21]>C(Cl)Cl>[N:10]1([CH:19]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:20]([OH:22])=[O:21])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8119AzepaneHCID 66827Phenylboronic AcidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 20992498HCID 20992498, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of phenylboronic acid (400 mg, 3.28 mmol), azepane (0.37 ml, 3.28 mmol) and 2-oxoacetic acid hydrate (302 mg, 3.28 mmol) dissolved in DCM (30 ml) was stirred at room temperature overnight. DCM was removed under vacuum and the crude was purified by flash chromatography (DCM/MeOH=8/2) to obtain the title compound (476 mg, 62.2% yield) as a white solid.

Workup

  1. customDCM was removed under vacuum
  2. customthe crude was purified by flash chromatography (DCM/MeOH=8/2)

Sources & evidence

ORD record
ord-1718f181117e4ca8848c1faa3454b3e8
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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