Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 66811027, compound

HRID 2099493Notes

Reaction equation

HRID 2099493 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:13]=[C:14]=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([O:29][C:14](=[O:15])[NH:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 574747361-Cyclohexyl-2-isocyanatobenzene

Product 1

HCID 66811027HCID 66811027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product of step (a) (˜9.8 mmol) and 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (2.4 g, 11.8 mmol) in DMF (19.7 mL) was stirred at room temperature for 24 h and then the solvent was removed under reduced pressure. The resulting residue was dissolved in ethyl acetate (20 mL) and this mixture was washed with 1N hydrochloric acid (2×10 mL), 1N aqueous sodium hydroxide (2×10 mL) and brine (10 mL), and then dried (MgSO4), filtered and the solvent removed under reduced pressure. The resulting residue was purified by column chromatography to give the title compound.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (20 mL)
  3. washthis mixture was washed with 1N hydrochloric acid (2×10 mL), 1N aqueous sodium hydroxide (2×10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-c35328e1ed514577b3e79fd05dacb026
Source dataset
uspto-grants-2009_08
Patent number
US07569586B2

Reaction notes

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