Sodium Azide → (+/-)-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide

HRID 13976Notes

Reaction equation

HRID 13976 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[O:17][C:16]3[C:18]4[CH2:19][CH2:20][CH2:21][C:22]=4[C:23]([Cl:25])=[CH:24][C:15]=3[CH2:14]2)(=O)=O)=CC=1.[N-:26]=[N+:27]=[N-:28].[Na+]>>[Cl:25][C:23]1[C:22]2[CH2:21][CH2:20][CH2:19][C:18]=2[C:16]2[O:17][CH:13]([CH2:12][N:26]=[N+:27]=[N-:28])[CH2:14][C:15]=2[CH:24]=1

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 86598582(+/-)-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86598581(+/-)-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide

Procedure

Treatment of (±)-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl 4-methylbenzenesulfonate (1.4 g, 3.70 mmol) with sodium azide (0.96 g, 14.78 mmol) generally according to the procedure described for Intermediate 24 gave (±)-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide as a crude oil. Treatment of the azide with sulfided platinum on carbon (5 wt. %, 0.15 g) generally according to the procedure described for Example 2 provided 0.74 g (77%) of (±)-1-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp 270° C. (dec); Anal. calcd. for C12H14ClNOHCl: C, 55.4; H, 5.81; N, 5.38. Found: C, 55.4; H, 5.8; N, 4.91.

Sources & evidence

ORD record
ord-b9121601e1f143d9bc614fd686dc1a52
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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