Bromoacetonitrile → HCID 67364717, compound

HRID 451697Notes

Reaction equation

HRID 451697 reaction equation
[OH:1][C@H:2]([C:16]1[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1)[C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[H-].[Na+].Br[CH2:26][C:27]#[N:28]>CC#N>[C:27]([CH2:26][O:1][C@@H:2]([C:16]1[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1)[C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:4]1)#[N:28]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 58017418HCID 58017418, compound

Product 1

HCID 67364717HCID 67364717, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-tert-butyl 3-((S)-hydroxy(m-tolyl)methyl)piperidine-1-carboxylate (30.5 g, 0.1 mol) in MeCN (300 mL), NaH (12 g, 0.3 mol) was added at 0° C. The mixture was stirred for 1 hr at rt. The mixture was cooled to −40° C., then bromoacetonitrile (35.7 g, 0.3 mol) was added in portions. The mixture was stirred for 0.5 hr at −20° C. continually. The reaction was quenched with sat. NH4Cl. The mixture was extracted with CH2Cl2. The organic layer was dried over Na2SO4, concentrated. Crude (R)-tert-butyl 3-((R)-(cyanomethoxy)(m-tolyl)methyl)piperidine-1-carboxylate was used for the next step without purification.

Workup

  1. temperatureThe mixture was cooled to −40° C.
  2. stirringThe mixture was stirred for 0.5 hr at −20° C. continually
  3. customThe reaction was quenched with sat. NH4Cl
  4. extractionThe mixture was extracted with CH2Cl2
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customCrude (R)-tert-butyl 3-((R)-(cyanomethoxy)(m-tolyl)methyl)piperidine-1-carboxylate was used for the next step without purification

Sources & evidence

ORD record
ord-d8af31c5956f42ea9bf195dd7cf94847
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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