4-Bromo-2-fluorobenzaldehyde → HCID 67224996, compound

HRID 500187Notes

Reaction equation

HRID 500187 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[NH:11]1[CH2:15][CH2:14][C@@H:13]([OH:16])[CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:15][CH2:14][C@@H:13]([OH:16])[CH2:12]2)=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 2759337(R)-3-PyrrolidinolHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67224996HCID 67224996, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-bromo-2-fluorobenzaldehyde (203.0 mg, 1.0 mmol) was mixed with (3R)-pyrrolidin-3-ol (87.1 mg, 1.0 mmol) in 1,2-dichloroethane (10 mL). The mixture was stirred at RT for 5 min, and then was treated with sodium triacetoxyborohydride (318 mg, 1.5 mmol). The mixture was stirred at RT for 2 h, and quenched by adding 1N NaOH. The organic phase was separated. The aqueous phase was extracted with methylene chloride. The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated to give the crude product (252 mg, 91.9%) which was directly used in next step without further purification. LCMS: (M+H)=275.9/273.9.

Workup

  1. stirringThe mixture was stirred at RT for 2 h
  2. customquenched
  3. additionby adding 1N NaOH
  4. customThe organic phase was separated
  5. extractionThe aqueous phase was extracted with methylene chloride
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1a5a098c8f8a4ce5abcc05bb88e70323
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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