Sodium hydride → HCID 86681278, compound

HRID 1467315Notes

Reaction equation

HRID 1467315 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][CH2:7][CH2:6][NH:5]1.Br[CH2:19][C:20]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=1[F:28]>CN(C)C=O>[F:28][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:20]=1[CH2:19][N:5]1[CH2:6][CH2:7][CH2:8][CH:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:4]1=[O:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27793222-Fluoro-6-methoxybenzyl bromideHCID 21260262tert-Butyl (2-oxopiperidin-3-yl)carbamate

Product 1

HCID 86681278HCID 86681278, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (82 mg, 2.054 mmol) was added to a solution of tert-butyl 2-oxopiperidin-3-ylcarbamate (200 mg, 0.933 mmol) in dimethylformamide (2 ml) at 23° C. and the resulting mixture was allowed to stir for 30 minutes. The mixture was then cooled to 0° C., and a solution of 2-(bromomethyl)-1-fluoro-3-methoxybenzene (214 mg, 0.977 mmol) in dimethylformamide (1.2 ml) added to the reaction mixture drop-wise. The resulting solution was allowed to stir for 90 minutes and was quenched with methanol. The mixture was then diluted with EtOAc, washed with water and brine, dried with magnesium sulfate, filtered and concentrated to afford tert-butyl 1-(2-fluoro-6-methoxybenzyl)-2-oxopiperidin-3-ylcarbamate. The crude product was progressed to the next step without purification.

Workup

  1. stirringto stir for 90 minutes
  2. customwas quenched with methanol
  3. additionThe mixture was then diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f75e2fdbb28e4b1ea58c9efd06a0720b
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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