(2-Bromoethyl)cyclohexane → HCID 67189860, compound

HRID 1258607Notes

Reaction equation

HRID 1258607 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:12])[O-:11])[CH:6]=[CH:5][CH:4]=1.[CH3:13][C:14]([CH3:17])([O-])[CH3:15].[K+].Br[CH2:20][CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C=O)C.C(OCC)(=O)C.O>[CH:22]1([CH2:21][CH2:20][N:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][OH:1])[N:8]=2)[C:10](=[O:11])[O:12][C:14]([CH3:17])([CH3:15])[CH3:13])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 3

HCID 15440(2-Bromoethyl)cyclohexaneHCID 23665647Potassium tert-butoxideHCID 86653154HCID 86653154, compound

Product 1

HCID 67189860HCID 67189860, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of [6-(hydroxymethyl)pyridin-2-yl]carbamate (200 mg, 1.07 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 ethyl acetate and water. The organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. Purification on silica gel afforded tert-butyl (2-cyclohexylethyl)[6-(hydroxymethyl)pyridin-2-yl]carbamate as a yellow oil [240 mg, yield 64%; HPLC/MS: m/z=335 (M+H); logP(HCOOH)=4.49]

Workup

  1. stirringAfter stirring at room temperature for 4 h
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-93240ac7f7674e6e80b1ee10d80087d6
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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