Boron tribromide → HCID 86760406, compound

HRID 348549Notes

Reaction equation

HRID 348549 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:13]2[CH2:18][CH2:17][N:16]([C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:13]2[CH2:14][CH2:15][N:16]([C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]3[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:17][CH2:18]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69417599HCID 69417599, compound

Product 1

HCID 86760406HCID 86760406, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (+/−)-4-methoxy-N-phenyl-N-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-benzenesulfonamide (0.047 g, 0.090 mmol) in dichloromethane (2 ml) was cooled to −78° C. Boron tribromide IM in dichloromethane (0.30 ml, 0.30 mmol) was added dropwise at this temperature. The mixture was then warmed to room temperature and stirred for 5 hours. The reaction was quenched with sodium hydroxyde 1N and extracted three times with dichloromethane. The combined organic phases were dried with sodium sulfate and concentrated. The residue was purified via flash chromatography on silica gel (dichloromethane/methanol/ammonia 110:10:1), yielding the title compound (0.029 mg, 63%) as an off-white solid, MS (ISP): m/e=491.3 (M+H+).

Workup

  1. customThe reaction was quenched with sodium hydroxyde 1N
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic phases were dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography on silica gel (dichloromethane/methanol/ammonia 110:10:1)

Sources & evidence

ORD record
ord-bbad9a4bfb5f42868e4c7c9531139024
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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