Dichloromethane → HCID 68949993, compound

HRID 2384932Notes

Reaction equation

HRID 2384932 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]2[CH2:15][N:14]([CH3:16])[CH2:13]2)=[O:11])=[CH:6][CH:5]=1.[CH2:17](Cl)Cl>>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:12]2[CH2:17][CH2:13][N:14]([CH3:16])[CH2:15]2)[OH:11])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 68948880HCID 68948880, compound

Product 1

HCID 68949993HCID 68949993, compoundYield 34%

Procedure

Add sodium tetrahydroborate (0.36 g, 9.52 mmol) in portions to a solution of (4-bromo-phenyl)-(1-methyl-azetidin-3-yl)-methanone (0.64 g, 2.38 mmol) in CH2Cl2 at 0° C. Stir the mixture at RT overnight and quench with water. Adjust the aqueous to pH=10 by using 1 N NaOH and extract with ethylacetate (2×150 mL). Dry the combined organic layers over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, collecting all the fractions as the product does not show by UV. Elute with 10% MeOH (2 N NH3)/CH2Cl2 to give 0.22 g (34%) of the title compound. LC-MS/ES m/z (79Br) 270.0 [M+H]+.

Workup

  1. customquench with water
  2. extractionextract with ethylacetate (2×150 mL)
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude material by flash chromatography
  7. customcollecting all the fractions as the product
  8. washElute with 10% MeOH (2 N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-1abbd5b64e974bfebd1c172efb562e96
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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