Benzyl Bromide → (1R*,4S*)-6-allyl-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene

HRID 13933Notes

Reaction equation

HRID 13933 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]2[C@H:10]3[CH2:16][C@H:7]([CH2:8][CH2:9]3)[C:6]=2[C:5]=1[OH:17])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([C:4]1[C:5]([O:17][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:6]2[C:11](=[C:12]([O:14][CH3:15])[CH:13]=1)[C@H:10]1[CH2:16][C@@H:7]2[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68583880(1R*,4S*)-6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ol

Product 1

HCID 68582937(1R*,4S*)-6-allyl-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthaleneYield 90.4%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

Treatment of (1R*,4S*)-6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ol (14.2 g, 61.66 mmol) with potassium carbonate (34.09 g, 0.247 mol), benzyl bromide (11.07 g, 64.74 mmol), and tetrabutylammonium iodide (0.224 g, 6.166 mmol) generally according to the procedure described for Intermediate 1 provided 17.86 g (90%) of (1R*,4S*)-6-allyl-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene as a colorless oil. Anal. calcd. for C22H2402-0.5H2O: C, 80.21; H, 7.65. Found: C, 79.81; H, 7.48.

Sources & evidence

ORD record
ord-076c36e468ba4c55807d39cb44c0cba6
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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