Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 59651891, compound

HRID 2042580Notes

Reaction equation

HRID 2042580 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[OH:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>CS(C)=O.ClCCl>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([O:15][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:6][N:7]=2)[CH2:17][CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 19604216HCID 19604216, compound

Product 1

HCID 59651891HCID 59651891, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To 6-(6-chloro-pyridin-3-yl)-4,5-dihydro-2H-pyridazin-3-one (3 g, 14.4 mmol) in DMSO (40 mL) was added 4-hydroxy-boc-piperidine (2.9 g, 14.4 mmol), followed by 1M KtOBu (19 mL). After overnight stirring at 100° C. open to air, the reaction was cooled, diluted with dichloromethane and washed several times with water/brine, dried over sodium sulfate, and concentrated under vacuum to obtain 4.9 g crude product (92%); MS m/z 373 (M+H).

Workup

  1. temperaturethe reaction was cooled
  2. washwashed several times with water/brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-104a3cb22ef74fbfa21d348fe102e252
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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