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

HRID 538772Notes

Reaction equation

HRID 538772 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-d2c89b3077414c43baf6491be7a69c3d
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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