Boron tribromide → HCID 18643845, compound

HRID 982128Notes

Reaction equation

HRID 982128 reaction equation
[NH2:1][C@H:2]1[C@H:13]2[C:14]3[C:5](=[CH:6][C:7]([O:21]C)=[CH:8][C:9]=3[CH2:10][C@@H:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12]2)[CH2:4][CH2:3]1.B(Br)(Br)[Br:24]>C(Cl)Cl>[BrH:24].[NH2:1][C@H:2]1[C@H:13]2[C:14]3[C:5](=[CH:6][C:7]([OH:21])=[CH:8][C:9]=3[CH2:10][C@@H:11]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57274359HCID 57274359, compound

Product 1

HCID 18643845HCID 18643845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.34 g (1.2 mmol) of [1R,8S,9aR] 1-amino-5-methoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene, from Step 7, in 9 mL of methylene chloride is treated with 4.4 mL (4.4 mmol) of a 1M solution of boron tribromide in methylene chloride, added dropwise at -78° C. The reaction is warmed to ambient temperature for 1 hour and recooled to -78° C. and the reaction is quenched with 5 mL of methanol. The reaction mixture is allowed to warm to ambient temperature and stirred for 1 hour. The solvent is removed in vacuo and 5 mL of methanol is added and the solution is concentrated to remove methyl borate by azeotropic distillation to give the title compound.

Workup

  1. additionadded dropwise at -78° C
  2. customrecooled to -78° C.
  3. customthe reaction is quenched with 5 mL of methanol
  4. temperatureto warm to ambient temperature
  5. customThe solvent is removed in vacuo and 5 mL of methanol
  6. additionis added
  7. concentrationthe solution is concentrated
  8. customto remove methyl borate
  9. distillationby azeotropic distillation

Sources & evidence

ORD record
ord-51581fb272cb412695b47e0a6e167218
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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