Boron tribromide → HCID 86609731, compound

HRID 2389946Notes

Reaction equation

HRID 2389946 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:16][CH:17]=3)[C@@H:12]3[CH2:29][CH2:30][CH2:31][N:11]3[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[N:23]1([CH2:22][CH2:21][CH2:20][O:19][C:15]2[CH:14]=[C:13]3[C:18]([C@H:9]([C:5]4[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=4)[CH2:10][N:11]4[CH2:31][CH2:30][CH2:29][C@H:12]43)=[CH:17][CH:16]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59383333HCID 59383333, compound

Product 1

HCID 86609731HCID 86609731, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-6-(3-methoxy-phenyl)-9-(3-piperidin-1-yl-propoxy)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline (27.0 mg, 0.042 mmol) in CH2Cl2 (0.2 mL) was added BBr3 (1 M in CH2Cl2, 0.21 mL) and the reaction mixture was stirred at rt for 15 min. The reaction was quenched with water and the mixture was concentrated under a stream of N2. The crude material was purified by reverse-phase HPLC to give 14.1 mg (53%) of the desired product as a TFA salt. MS: exact mass calcd for C26H34N2O2, 406.3; m/z found, 407.5 [M+H]+. 1H NMR (acetone-d6): 7.20 (m, 1H), 6.92 (m, 1H), 6.78 (m, 5H), 4.83 (m, 1H), 4.46 (m, 1H), 4.11 (t, J=7.2, 2H), 3.87 (m, 1H), 3.59 (m, 2H), 3.38 (m, 2H), 3.28 (m, 2H), 2.89 (m, 3H), 2.87 (m, 2H), 2.29 (m, 5H), 1.88 (m, 4H), 1.57 (m, 2H).

Workup

  1. customThe reaction was quenched with water
  2. concentrationthe mixture was concentrated under a stream of N2
  3. customThe crude material was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-8b6bdcc96d9545848a1987b5d76e15ac
Source dataset
uspto-grants-2012_09
Patent number
US08273762B2

Reaction notes

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