Boron tribromide → HCID 57504905, compound

HRID 2060774Notes

Reaction equation

HRID 2060774 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]23[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:12][S:11][C:10]([NH2:17])=[N:9]3)=[CH:4][C:3]=1[O:18]C.B(Br)(Br)Br>C(Cl)Cl.O>[NH2:17][C:10]1[S:11][CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][C@:8]2([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([OH:18])[CH:4]=2)[N:9]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 57504903HCID 57504903, compound

Product 1

HCID 57504905HCID 57504905, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of (7aS)-7a-(4-fluoro-3-methoxyphenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-amine (0.717 g, 2.56 mmol) in CH2Cl2 (15 mL) is added boron tribromide 11.20 g, 7.67 mmol). The reaction is warmed to 0° C. and is stirred for 2 hr. The reaction is diluted with water and the pH is adjusted to 7. The aqueous is extracted three times with EtOAc (some MeOH is added to help dissolve some solids during the extraction). The organic layer is dried over Na2SO4 and the solvent is removed under reduced pressure. The crude product is purified with a 10 g SCX column using 4:1 CH2Cl2:MeOH and then 2:1 CH2Cl2:7 N NH3 in MeOH to elute the product and give the title compound (0.56 g, 82%). ES/MS m/e: 267 (M+1).

Workup

  1. extractionThe aqueous is extracted three times with EtOAc (some MeOH
  2. additionis added
  3. dissolutionto help dissolve some solids
  4. extractionduring the extraction)
  5. dry with materialThe organic layer is dried over Na2SO4
  6. customthe solvent is removed under reduced pressure
  7. customThe crude product is purified with a 10 g SCX column
  8. washMeOH and then 2:1 CH2Cl2:7 N NH3 in MeOH to elute the product

Sources & evidence

ORD record
ord-163718f9dd7a40eeae553094a20bd1f2
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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