Hexane → HCID 10045213, compound

HRID 1951316Notes

Reaction equation

P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CCCCCC.O(C(C)(C)C)[Na].[CH3:26][O:27][C:28]1[CH:29]=[CH:30][C:31]2[CH2:32][C@H:33]3[NH:44][CH2:43][CH2:42][C@@:39]4([C:40]=2[CH:41]=1)[C@H:34]3[CH2:35][CH2:36][CH2:37][CH2:38]4.[N+:45]([C:48]1[CH:53]=[CH:52][C:51](Br)=[CH:50][CH:49]=1)([O-:47])=[O:46]>C1(C)C=CC=CC=1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:26][O:27][C:28]1[CH:29]=[CH:30][C:31]2[CH2:32][C@H:33]3[N:44]([C:51]4[CH:52]=[CH:53][C:48]([N+:45]([O-:47])=[O:46])=[CH:49][CH:50]=4)[CH2:43][CH2:42][C@@:39]4([C:40]=2[CH:41]=1)[C@H:34]3[CH2:35][CH2:36][CH2:37][CH2:38]4

Participants

Conditions

Temperature: 80 °C

Procedure

Pd(OAc)2 (1.34 mg, 0.006 mmol) and 10% solution of P(t-Bu)3 in hexane (0.015 ml, 0.0048 mmol) were added to the suspension of NaO-t-Bu (86.4 g, 0.9 mmol), (+)-3-methoxy-morphinan (0.1645 g, 0.5 mmol) and 4-(nitro)bromobenzene (0.1212 g, 0.6 mmol) in toluene (˜12 mL) in the presence of nitrogen. The resulting mixture was heated at 80° C. for 6 h. The reaction mixture was allowed to cool to room temperature, diluted with methylene chloride (50 mL), and washed with water. Concentration of the organic layer and flash chromatography on silica gel was carried out eluting with hexane first and then with a 5% to 20% ethyl acetate solution in hexane to provide a yellow liquid, 56.4 mg (30% yield); ms (EI): m/z 378 (M).

Workup

temperatureto cool to room temperature
washwashed with water
washConcentration of the organic layer and flash chromatography on silica gel was carried out eluting with hexane first
customwith a 5% to 20% ethyl acetate solution in hexane to provide a yellow liquid, 56.4 mg (30% yield)

Sources & evidence

ORD record: ord-214f60f92c08415f863c99dd4e578134
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404706B2

Reaction notes

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