Aluminium lithium hydride → (+/-)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)-N-methylmethanamine

HRID 13975Notes

Reaction equation

HRID 13975 reaction equation
[Cl:1][C:2]1[C:13]2[CH2:12][CH:11]([CH2:14][NH:15][C:16](=O)OC)[O:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Cl:1][C:2]1[C:13]2[CH2:12][CH:11]([CH2:14][NH:15][CH3:16])[O:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86598562(+/-)-methyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate

Product 1

HCID 11368394(+/-)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)-N-methylmethanamineYield 30%

Procedure

Treatment of (±)-methyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate (0.60 g, 2.12 mmol) with lithium aluminum hydride (95 wt. %, 0.35 g, 8.75 mmol) generally according to the procedure described for Example 24 provided 0.15 g (30%) of (±)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)-N-methylmethanamine as a white solid. mp 58-60° C.; Anal. calcd. for C13H16ClNO: C, 65.68; H, 6.78; N, 5.89. Found: C, 65.31; H, 6.79; N, 5.52.

Sources & evidence

ORD record
ord-6bd5c90f6bea4e32a25b2e7fad407712
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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