Triethylamine → cis-3,8-Dimethyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

HRID 1714150Notes

Reaction equation

HRID 1714150 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[CH2:13][C@H:12]1[C@@H:7]2[CH2:8][NH:9][CH2:10][CH2:11]1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].CCN(CC)CC>C(Cl)Cl>[CH3:16][N:9]1[CH2:8][C@H:7]2[C@H:12]([CH2:13][C:14]3[C:6]2=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])[CH2:11][CH2:10]1.[CH2:19]([O:18][C:16]([N:9]1[CH2:8][C@H:7]2[C@H:12]([CH2:13][C:14]3[C:6]2=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])[CH2:11][CH2:10]1)=[O:17])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16117548cis-8-Methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

Product 2

HCID 16117682cis-3,8-Dimethyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoreneHCID 86611064cis-8-Methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (9.0 mg, 0.044 mmol) was prepared by following the procedure of example 17. cis-8-Methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (16 mg, 0.085 mmol) was reacted with ethyl chloroformate (18.5 mg, 0.17 mmol) and Et3N (43 mg, 0.43 mmol) in CH2Cl2 (0.5 mL) to give cis-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (12 mg, 0.046 mmol) which was reduced with LiAlH4 (3.5 mg, 0.093 mmol) in THF (1 mL): MS (ES) 202.2 (M+H).

Sources & evidence

ORD record
ord-d738f575107848e7a714aff16f940529
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

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