Water → HCID 24902440, compound

HRID 1744237Notes

Reaction equation

HRID 1744237 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].F[C:18]1[CH:19]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:22][CH:23]=1.O>CN1C(=O)CCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67867alpha,alpha,alpha,3-TetrafluorotolueneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 24902440HCID 24902440, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Sodium hydride (0.9 g, 60% dispersion in mineral oil) was added to a solution of 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (4 g) in NMP (40 ml) and the solution stirred for 1 h, then a solution of 3-fluorobenzotrifluoride (3.5 g) in NMP (10 ml) was added and the mixture was stirred for 2 h at 80 ° C. The mixture was added to water (200 ml) and extracted with diethyl ether (2×100 ml), the solvent washed with water, 1 M sodium hydroxide and brine, dried and evaporated to give the title compound as yellow oil (5.2 g) which was carried through to the next step without purification.

Workup

  1. stirringthe mixture was stirred for 2 h at 80 ° C
  2. extractionextracted with diethyl ether (2×100 ml)
  3. washthe solvent washed with water, 1 M sodium hydroxide and brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ebdb5f2b884b418c98f7a9c2dcc357eb
Source dataset
uspto-grants-2006_03
Patent number
US07015234B2

Reaction notes

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