HCID 86599174, compound → HCID 68961625, compound

HRID 2116100Notes

Reaction equation

HRID 2116100 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[C:7]=2[O:6]1)=[N+]=[N-]>[Pd]>[CH:14]1([C:13]2[C:7]3[O:6][CH:5]([CH2:4][NH2:1])[CH2:9][C:8]=3[CH:10]=[CH:11][CH:12]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

3

Reactant 1

HCID 86599174HCID 86599174, compound

Product 1

HCID 68961625HCID 68961625, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(7-cyclopentyl-2,3-dihydro-1-benzofuran-2-yl)methanol (4.08 g, 18.7 mmol) with p-toluenesulfonyl chloride (3.92 g, 21.9 mmol) in anhydrous pyridine (76 mL) generally according to the procedure described for Intermediate 10 gave (±)-(7-cyclopentyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a tan oil. Treatment of the tosylate with sodium azide (4.39 g, 67.57 mmol) generally according to the procedure described for Intermediate 98 afforded 4.1 g of (±)-2-(azidomethyl)-7-cyclopentyl-2,3-dihydro-1-benzofuran as a yellow oil. Treatment of the azide with palladium on carbon (0.41 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 2.5 g (58%) of (±)-(7-cyclopentyl-2,3-dihydro-1-benzofuran-2-yl)methylamine as a white solid, hydrochloride salt. mp 174° C.; Anal. calcd. for C14H900N2HCl: C, 66.26; H, 7.94; N, 5.52. Found C, 66.13; H, 7.71; N, 5.5.

Sources & evidence

ORD record
ord-7f6f5f3913674b769382244fa98aec0a
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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