Triacetoxyperiodinane → HCID 58243410, compound

HRID 2361670Notes

Reaction equation

HRID 2361670 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:17][CH:16]([OH:18])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:15][C:16](=[O:18])[CH2:17]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 44462713HCID 44462713, compound

Product 1

HCID 58243410HCID 58243410, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-ol (27 mg, 0.11 mmol) in dichloromethane (2 ml) was added Dess Martin periodinane (80 mg, 0.19 mmol) at room temperature. The mixture was stirred for 3 hours and then concentrated and purified by FCC (eluting with DCM/MeOH/NH3 gradient 95:5:1 to 90:10:1) to provide the title compound as colourless oil (17 mg, 63%).

Workup

  1. concentrationconcentrated
  2. custompurified by FCC (eluting with DCM/MeOH/NH3 gradient 95:5:1 to 90:10:1)

Sources & evidence

ORD record
ord-cc51a79c6a594b27b997a65568b46f2c
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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