Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 59652002, compound

HRID 2042584Notes

Reaction equation

HRID 2042584 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[N:13]=2)=[CH:4][CH:3]=1.[OH:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1>C1(C)C=CC=CC=1>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([O:16][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[N:13]=3)=[CH:6][N:7]=2)[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 59652048HCID 59652048, compound

Product 1

HCID 59652002HCID 59652002, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To 6-(6-chloro-pyridin-3-yl)-2-methyl-2H-pyridazin-3-one (3 g, 13.6 mmol) in toluene (50 mL) was added 4-hydroxy-boc-piperidine (2.7 g, 13.6 mmol) and 1M KtOBu (16.3 mL, 16.3 mmol). After overnight stirring at 80° C., the reaction was concentrated, partitioned between dichloromethane/1N sodium carbonate, washed with water/brine, dried over sodium sulfate, and concentrated. The product was purified by column chromatography (99:1 dichloromethane:methanol) to obtain 2.7 g (51%); MS m/z 387 (M+H).

Workup

  1. concentrationthe reaction was concentrated
  2. custompartitioned between dichloromethane/1N sodium carbonate
  3. washwashed with water/brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography (99:1 dichloromethane:methanol)
  7. customto obtain 2.7 g (51%)

Sources & evidence

ORD record
ord-89dcc3702de94aa889a97933572e4340
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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