Boron tribromide → 2-[(6bR,10aS)-1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole-5-yl]phenol

HRID 1764921Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([O:18][CH2:19][CH2:20][N:14]3[C@H:13]3[CH2:21][CH2:22][NH:23][CH2:24][C@@H:12]23)[CH:17]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:20]1[N:14]2[C:15]3[C:11]([C@@H:12]4[CH2:24][NH:23][CH2:22][CH2:21][C@@H:13]42)=[CH:10][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])=[CH:17][C:16]=3[O:18][CH2:19]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of (6bR,10aS)-5-(2-methoxyphenyl)-1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole (20 mg, 0.06 mmol) in CH2Cl2 (4 mL) under N2 was added a 0.91 M solution of BBr3 in CH2Cl2 (0.41 mL, 0.37 mmol). The reaction mixture was stirred at 20° C. for 16 h, and then quenched with water (1 mL). The aqueous layer was basified with 1 N NaOH to pH 7, and the reaction mixture was extracted with CH2Cl2 (3×30 mL). The organic solution was then dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow oil (10 mg, 50%). 1H NMR (CDCl3) δ1.88-2.01 (m, 2H), 2.10-2.22 (m, 1H), 2.60-2.79 (m, 2H), 2.90-2.99 (m, 1H), 3.18-3.37 (m, 3H), 3.36-3.43 (m, 2H), 3.61-3.66 (m, 1H), 4.39-4.44 (m, 2H), 6.70-6.79 (m, 1H), 6.80-6.99 (m, 2H), 7.08-7.18 (m, 2H) ppm.

Workup

customquenched with water (1 mL)
extractionthe reaction mixture was extracted with CH2Cl2 (3×30 mL)
dry with materialThe organic solution was then dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-47b3f1686aef4534aeba0c5283c144b4
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039679E1

Reaction notes

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