(2-Bromoethyl)cyclohexane → HCID 67425832, compound

HRID 2039678Notes

Reaction equation

HRID 2039678 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:24][CH2:25][CH:26]1CC[CH2:29][CH2:28][CH2:27]1>CN(C=O)C.O>[CH2:24]([N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[N:9]=1)[C:6](=[O:16])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 15440(2-Bromoethyl)cyclohexaneHCID 19349090Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67425832HCID 67425832, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl[6-(hydroxymethyl)pyridin-2-yl]carbamate (3.79 g, 16.9 mmol) in DMF, cooled to 0° C. with a brine/ice bath, was added potassium tert-butoxide (126 mg, 1.07 mmol). The mixture was stirred 5 minutes at 0° C. then 1-bromo-2cyclohexylethane (205 mg, 1.07 mmol) was added. After stirring at room temperature for 4 h, the reaction mixture was diluted with water (200 mL), extracted with ethyl acetate (150 mL). The organic layer was washed with water, dried (MgSO4) and concentrated in vacuo. Purification on silica gel afforded tert-butyl hexyl[6-(hydroxymethyl)pyridin-2-yl]carbamate as a yellow oil [3.60 g, yield 69%; HPLC/MS: m/z=309 (M+H); log P(HCOOH)=3.94].

Workup

  1. stirringAfter stirring at room temperature for 4 h
  2. extractionextracted with ethyl acetate (150 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-b22fc63d0d0a42aba4e969455ddd4d12
Source dataset
uspto-grants-2013_11
Patent number
US08580799B2

Reaction notes

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