Aluminium lithium hydride → trans-(11-Aminomethyl-8-chloro-10,11-dihydro-dibenzo[b,f]oxepin-10-yl)-methanol

HRID 243630Notes

Reaction equation

HRID 243630 reaction equation
C[O:2][C:3]([C@@H:5]1[C:11]2[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=2[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[C@H:6]1[CH2:21][N+:22]([O-])=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.C1(C)C=CC=CC=1>C1COCC1>[NH2:22][CH2:21][C@H:6]1[C@H:5]([CH2:3][OH:2])[C:11]2[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=2[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 22635083Tetrahydrofuran tolueneHCID 59800204Trans-8-chloro-11-nitromethyl-10,11-dihydro-dibenzo[b,f]oxepine-10-carboxylic acid methyl ester

Product 1

HCID 56652617trans-(11-Aminomethyl-8-chloro-10,11-dihydro-dibenzo[b,f]oxepin-10-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-8-Chloro-11-nitromethyl-10,11-dihydro-dibenzo[b,f]oxepine-10-carboxylic acid methyl ester (8) (5.0 g, 13.23 mmol) in dry THF (25 ml) is added at −15° C. to a mixture of THF (25 ml) and 3.5 M LAH suspension in THF/Toluene (16.4 ml, 57.5 mmol).

Sources & evidence

ORD record
ord-884229bc3b9341bc9cdd35c805d79e02
Source dataset
uspto-grants-2014_02
Patent number
US08653280B2

Reaction notes

Loading…