4-Toluenesulfonyl chloride → HCID 86599173, compound

HRID 2116099Notes

Reaction equation

HRID 2116099 reaction equation
[CH:1]1([C:6]2[C:14]3[O:13][CH:12]([CH2:15][OH:16])[CH2:11][C:10]=3[CH:9]=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:16][CH2:15][CH:12]2[CH2:11][C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[C:14]=3[O:13]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68963161HCID 68963161, compound

Product 1

HCID 86599173HCID 86599173, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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-92dae1dacd9543b6af20ff2b99eb5816
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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