Iodine → 1-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)cyclobutanol

HRID 254631Notes

Reaction equation

HRID 254631 reaction equation
[NH2:1][CH2:2][C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.[CH3:8][C:9]([CH3:14])([CH3:13])[CH2:10][CH:11]=O.[S-:15][C:16]#[N:17].[K+].II>C(#N)C>[C:9]([C:10]1[S:15][C:16](=[NH:17])[N:1]([CH2:2][C:3]2([OH:7])[CH2:6][CH2:5][CH2:4]2)[CH:11]=1)([CH3:14])([CH3:13])[CH3:8]

Participants

6

Reactant 4

HCID 807IodineHCID 763353,3-DimethylbutanalHCID 516872Potassium thiocyanateHCID 282600091-(Aminomethyl)cyclobutan-1-ol

Product 1

HCID 668520141-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)cyclobutanolYield 32.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(aminomethyl)cyclobutanol (prepared from cyclobutanone as described in WO 2006/100208) (7.2 g, 71 mmol), 3,3-dimethylbutanal (9.8 mL, 78 mmol), 4 Å molecular sieves (10 g, 8-12 mesh beads), potassium thiocyanate (9.2 g, 95 mmol) and iodine (18 g, 71 mmol) in acetonitrile (100 mL) were processed as described in Example 18A to provide the title compound (5.5 g, 23 mmol, 32% yield). MS (DCI/NH3) m/z 241 (M+H)+.

Sources & evidence

ORD record
ord-d1cf70cfa3cc41eda4a0e04bf68a60f9
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

Loading…