Aluminium lithium hydride → cis-Benzyl-(3,8-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoren-6-yl)-amine

HRID 1714154Notes

Reaction equation

HRID 1714154 reaction equation
C(O[C:4]([N:6]1[CH2:18][C@H:17]2[C@H:9]([CH2:10][C:11]3[C:16]2=[CH:15][C:14]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][C:12]=3[CH3:27])[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:20]([NH:19][C:14]1[CH:15]=[C:16]2[C:11](=[C:12]([CH3:27])[CH:13]=1)[CH2:10][C@H:9]1[C@@H:17]2[CH2:18][N:6]([CH3:4])[CH2:7][CH2:8]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86611066cis-6-Benzylamino-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester

Product 1

HCID 16117812cis-Benzyl-(3,8-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoren-6-yl)-amineYield 8.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound (5.0 mg, 0.016 mmol) was prepared by following the procedure of step B of example 17 from crude cis-6-benzylamino-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (66 mg, 0.18 mmol) and LiAlH4 (27 mg, 0.73 mmol) in THF (1 mL): MS (ES) 307.2 (M+H).

Sources & evidence

ORD record
ord-b821514a986e42e4b5aeb18389575453
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

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