Hydrochloric Acid → HCID 12985405, compound

HRID 2184664Notes

Reaction equation

HRID 2184664 reaction equation
[Br:1][CH2:2][C:3](=[O:15])[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[BH4-].[Na+].C(OCC)(=O)C.Cl>O1CCCC1.CO>[OH:15][CH:3]([CH2:2][Br:1])[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 12985404HCID 12985404, compound

Product 1

HCID 12985405HCID 12985405, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of step 1 (500 mg, 1.84 mmoles) was dissolved in a mixture of tetrahydrofuran (9 mL) and methanol (1 mL), the solution was cooled in an ice-bath, and sodium borohydride (72 mg, 1.90 mmoles) was added in one portion. Stirring was continued in the ice-bath for 15 min, and ethyl acetate (50 mL) and M hydrochloric acid (1.5 mL) were added. The aqueous layer was separated, extracted with ethyl acetate (20 mL), and the combined organic layers were washed with saturated sodium bicarbonate (40 mL), dried over anhydrous magnesium sulfate and evaporated to give benzyl 3-hydroxy-4-bromobutanoate (433 mg, 86%). 1HMR (CDCl3, δ): 7.36 (5H, s), 5.17 (2H, s), 4.26 (1H, m), 3.50 (1H, dd, 5.0, 10.5 Hz), 3.47 (1H, dd, 5.6, 10.5 Hz), 3.06 (1H, d, 541 Hz), 2.72 (1H, dd, 5.0, 16.6 Hz), 2.69 (1H, dd, 7.3, 16.6 Hz). IR (neat): 3443, 3064, 1731, 1624 cm−1. Mass spectum (CI,m/z): 273, 275 (M+1, M+3). Calcd. for C11H13BrO3.0.5H2O: C 53.75; H 5.88. Found: C 53.65; H 5.60.

Workup

  1. temperaturethe solution was cooled in an ice-bath
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (20 mL)
  4. washthe combined organic layers were washed with saturated sodium bicarbonate (40 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-7d0c34109882442780c4870c76305997
Source dataset
uspto-grants-2002_06
Patent number
US06399600B1

Reaction notes

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