Water → HCID 59652023, compound

HRID 2042586Notes

Reaction equation

HRID 2042586 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[C:16]1[N:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1.O>CS(C)=O>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([O:1][C:16]2[CH:17]=[CH:18][C:19]([C:22](=[O:24])[CH3:23])=[CH:20][N:21]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 59652023HCID 59652023, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To 4-hydroxy-boc-piperidine (1.55 g, 7.71 mmol) in DMSO (12 mL) was added 1M KtOBu (8.36 mL), followed by 1-(6-chloropyridin-3-yl)ethanone (1.00 g, 6.43 mmol). After overnight stirring at 100° C., the reaction was poured into water, extracted with dichloromethane, washed with brine, dried over sodium sulfate, and concentrated. The product was purified using a Single Step column (7:3 hexanes:ethyl acetate) to obtain 0.5 g (25%); MS m/z 321 (M+H).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product was purified
  6. customto obtain 0.5 g (25%)

Sources & evidence

ORD record
ord-f1c875b63aa94766bb16579cddade029
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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