Acetone Cyanohydrin → HCID 90303212, compound

HRID 1051928Notes

Reaction equation

HRID 1051928 reaction equation
[S:1]1[C:5]2[CH:6](O)[CH2:7][CH2:8][O:9][C:4]=2[N:3]=[CH:2]1.CC(C)(O)[C:13]#[N:14].P(CCCC)(CCCC)CCCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1.C(OC(C)C)(C)C>[S:1]1[C:5]2[CH:6]([C:13]#[N:14])[CH2:7][CH2:8][O:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 6406Acetone CyanohydrinHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 90303245HCID 90303245, compound

Product 1

HCID 90303212HCID 90303212, compound

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 6,7-dihydro-5H-pyrano[2,3-d]thiazol-7-ol (0.65 g, 4.14 mmol), acetone cyanohydrin (880 mg, 10.3 mmol) and (n-Bu)3P (1.67 g, 8.27 mmol) in THF (79 mL) was added at 0° C. 1,1′-(azodicarbonyl)dipiperidine (2.09 g, 8.27 mmol). The mixture was stirred at 0° C. for 30 min, then, it was allowed to warm to RT and was stirred for 2 h. Subsequently, the reaction mixture was diluted with diisopropyl ether, filtrated and the filtrate was conc. in vacuo. Purification by means of CC (5-70% EtOAc/Hept) provided a yellow solid.

Workup

  1. additionwas added at 0° C
  2. temperatureto warm to RT
  3. stirringwas stirred for 2 h
  4. filtrationfiltrated
  5. customPurification by means of CC (5-70% EtOAc/Hept)
  6. customprovided a yellow solid

Sources & evidence

ORD record
ord-2db5a96026d5415e9c1cc21caca724ad
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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