Bromoacetonitrile → HCID 67364383, compound

HRID 451991Notes

Reaction equation

HRID 451991 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([OH:23])[C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].Br[CH2:27][C:28]#[N:29]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([O:23][CH2:27][C:28]#[N:29])[C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 11534Bromoacetonitrile2×HCID 24758Sodium hydride2×HCID 58017385HCID 58017385, compound

Product 1

HCID 67364383HCID 67364383, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of (R)-tert-butyl 3-((R)-(3-chloro-4-fluorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (5.1 g, 15 mmol) in CH3CN (150 mL), NaH (1.8 g, 45 mmol) was added at 0° C. The mixture was stirring for 1 hour. Then the mixture was cooled to −40° C., the bromoacetonitrile (5.4 g, 45 mmol) was added dropwise. The mixture was allowed to warm to 0° C. gradually. The addition of NaH and bromoacetonitrile was repeated three times. The mixture was quenched with H2O and exacted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrate to get the crude (R)-tert-butyl 3-((R)-(3-chloro-4-fluorophenyl)(cyanomethoxy)methyl)piperidine-1-carboxylate (6.5 g, 100%).

Workup

  1. temperatureto warm to 0° C. gradually
  2. customThe mixture was quenched with H2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-b70b73cbecd34d3e89b8cf3a5aa894ff
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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