Hydrogen Bromide → (2R)-2-bromo-2-cyclohexylacetic acid

HRID 132985Notes

Reaction equation

HRID 132985 reaction equation
N[C@H:2]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].[BrH:12].N([O-])=O.[Na+]>O>[Br:12][C@H:2]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 736849Cyclohexylglycine, (R)-HCID 23668193Sodium Nitrite

Product 1

HCID 36690978(2R)-2-bromo-2-cyclohexylacetic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The (R)-2-amino-2-cyclohexylacetic acid (H-Cyclohexyl-D-Gly-OH, 1 g, 6.36 mmol), which is commercially available from Bachem California Inc., Torrance, Calif. 90505, was dissolved in a mixture of HBr 48% (5.8 niL, 50.9 mmol) and H2O (20 mL). At 0° C., a solution of NaNO2 (1.4 g, 20.4 mmol) in H2O (10 mL) was added over a period of 30 min. The reaction was stirred for two hours. The reaction mixture was degassed in vacuo and extracted with EtOAc (2×2mL). The extracts were washed with water (15 mL), dried (Na2SO4), filtered and evaporated to give 1.3 g (92% yield) of the (R)-2-bromo-2-cyclohexylacetic acid as a white solid.

Workup

  1. customThe reaction mixture was degassed in vacuo
  2. extractionextracted with EtOAc (2×2mL)
  3. washThe extracts were washed with water (15 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-40a05c89549d411180730537a45089f9
Source dataset
uspto-grants-2008_06
Patent number
US07390789B2

Reaction notes

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