Sodium Hydroxide → HCID 59808798, compound

HRID 1887985Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:12]2(O)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[OH-].[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]=2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 57445556HCID 57445556, compound

Product 1

HCID 59808798HCID 59808798, compoundYield 89.9%

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl 4-[3-fluoro-5-(methylsulfonyl)phenyl]-4-hydroxypiperidine-1-carboxylate (3.3 g, 8.8 mmol) and polyphosphoric acid (20 ml) was heated at 120° C. for 3 h. The mixture was poured on to ice and was basified with 5 M sodium hydroxide. The mixture was extracted with ethylacetate (3×100 ml) and the combined organic phases was dried (MgSO4), evaporated and purified by flash column chromatography (methanol/ethylacetate 1:1) to give the title compound (2.02 g). MS m/z (rel. intensity, 70 eV) 255 (M+, bp), 254 (50), 251 (87), 172 (87), 146 (53).

Workup

additionThe mixture was poured on to ice
extractionThe mixture was extracted with ethylacetate (3×100 ml)
dry with materialthe combined organic phases was dried (MgSO4)
customevaporated
custompurified by flash column chromatography (methanol/ethylacetate 1:1)

Sources & evidence

ORD record: ord-821080415fa3455aac39517a9b295420
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501777B2

Reaction notes

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