Triphenylphosphine → (+/-)-1-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine

HRID 2116179Notes

Reaction equation

HRID 2116179 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(/C=C/C(C)(C)C)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[CH3:32][C:33]([CH3:50])([CH3:49])/[CH:34]=[CH:35]/[C:36]1[C:44]2[O:43][CH:42]([CH2:45][N:46]=[N+]=[N-])[CH2:41][C:40]=2[CH:39]=[CH:38][CH:37]=1.[N-]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH3:32][C:33]([CH3:50])([CH3:49])/[CH:34]=[CH:35]/[C:36]1[C:44]2[O:43][CH:42]([CH2:45][NH2:46])[CH2:41][C:40]=2[CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 33558AzideHCID 86599128HCID 86599128, compoundHCID 86599236(+/-)-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide

Product 1

HCID 68961708(+/-)-1-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methanamineYield 28%

Procedure

Treatment of (±)-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methyl 4-methylbenzenesulfonate (6.54 g, 16.92 mmol) with sodium azide (4.37 g, 67.68 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide. Treatment of the azide (1.78 g, 6.92 mmol) with triphenylphosphine (1.81 g, 6.92 mmol) generally according to the procedure described for Example 21 afforded 0.454 g (28%) of (±)-1-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine as a white solid, hydrochloride salt. mp 216-218° C.; Anal. calcd. for C15H21NOHCl: C, 67.28; H, 8.28; N, 5.23. Found: C, 66.19; H, 8.27; N, 5.14.

Sources & evidence

ORD record
ord-909cd190076e4e288fad1de0a6109faf
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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