Methanol → HCID 178514177, compound

HRID 1596614Notes

Reaction equation

HRID 1596614 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:11][C@H:10]([NH:12][OH:13])[CH2:9]2)=[CH:4][CH:3]=1.C[Si]([N:18]=[C:19]=[S:20])(C)C.CO>C1COCC1>[OH:13][N:12]([C@H:10]1[CH2:11][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9]1)[C:19]([NH2:18])=[S:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 75297IsothiocyanatotrimethylsilaneHCID 178526348HCID 178526348, compound

Product 1

HCID 178514177HCID 178514177, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of cis-3-(4-fluorophenyl)cyclobutylhydroxylamine (1.81 g, 10 mmol) in THF (30 ml) was added trimethylsilylisothiocyanate (1.58 g, 12 mmol) at room temperature. After stirring for 3 hours at 70° C., MeOH (20 ml) was added. Volatiles were removed in vacuo, and the residue recrystallized from ethyl acetate/n-hexane/EtOH to afford 1.34 g (55.8% yield) of the title compound, m.p. 156-158° C.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue recrystallized from ethyl acetate/n-hexane/EtOH

Sources & evidence

ORD record
ord-b3916edf005a40af81023762ace36818
Source dataset
uspto-grants-2001_09
Patent number
US06291520B1

Reaction notes

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