Hexane → HCID 10065431, compound

HRID 908367Notes

Reaction equation

HRID 908367 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([C:20]4[CH:25]=[CH:24][C:23]([N+]([O-])=O)=[CH:22][CH:21]=4)[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CCCCCC.O(C(C)(C)C)[Na]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4

Participants

6

Reactant 4

HCID 8058HexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 10045213HCID 10045213, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 10065431HCID 10065431, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Similar to the preparation of the compound of Example 13, the title compound is made from the reaction of Pd(OAc)2 (1.34 mg, 0.006 mmol), 10% solution of P(t-Bu)3 in hexane (0.015 ml, 0.0048 mmol), and NaO-t-Bu (86.4 g, 0.9 mmol) in the presence of argon and then a solution of (+)-3-methoxy-morphinan (0.1645 g, 0.5 mmol) and bromobenzene (0.094 g, 0.6 mmol) in toluene (˜12 mL).

Sources & evidence

ORD record
ord-b5afdeeb7ba94858ab1c7680d085c231
Source dataset
uspto-grants-2011_09
Patent number
US08017622B2

Reaction notes

Loading…