Boron tribromide → HCID 19029130, compound

HRID 2256060Notes

Reaction equation

HRID 2256060 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[C:21]([O:23]C)[CH:20]=[CH:19][C:18]=2[O:25]C)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[OH:25][C:18]1[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:17]=1[CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19029160HCID 19029160, compound

Product 1

HCID 19029130HCID 19029130, compoundYield 143.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-benzyloxycarbonyl-4-(2,5-dimethoxyphenyl)piperidine (0.54 g), prepared as described in Example 21.b., in 10 mL of dichloromethane, was cooled to 0° C. and treated with a solution of boron tribromide in dichloromethane (1.0M, 9 mL). After stirring for 1 hour at 0° C., the reaction mixture was allowed to warm to room temperature. At the end of the period, the reaction mixture was cooled to 0° C. and quenched with methanol. The resulting solution was evaporated and then treated with additional amounts of methanol. After evaporation the product was obtained as a yellow solid (0.42 g); MS: 194; NMR: 1.6-1.9 (m, 4), 3.0 (m, 2), 3.3 (br, 2), 6.4-6.5 (m, 2), 6.6 (d, J=8, 1), 8.3-8.8 (m, 3).

Workup

  1. temperatureto warm to room temperature
  2. temperatureAt the end of the period, the reaction mixture was cooled to 0° C.
  3. customquenched with methanol
  4. customThe resulting solution was evaporated
  5. additiontreated with additional amounts of methanol
  6. customAfter evaporation the product

Sources & evidence

ORD record
ord-2f80e266964145c3ab3701d265bb7254
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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