Ethyl chloroformate → cis-6-Bromo-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester

HRID 1714152Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C([N:14]1[CH2:26][C@H:25]2[C@H:17]([CH2:18][C:19]3[C:24]2=[CH:23][C:22]([Br:27])=[CH:21][C:20]=3[CH3:28])[CH2:16][CH2:15]1)C1C=CC=CC=1>C1COCC1>[CH2:5]([O:4][C:2]([N:14]1[CH2:26][C@H:25]2[C@H:17]([CH2:18][C:19]3[C:24]2=[CH:23][C:22]([Br:27])=[CH:21][C:20]=3[CH3:28])[CH2:16][CH2:15]1)=[O:3])[CH3:6]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of ethyl chloroformate (293 mg, 2.7 mmol) in THF (1.5 mL) was added a solution of cis-3-benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (320 mg, 0.90 mmol) in dry THF (1.5 mL) dropwise over 10 min at 0° C. The reaction mixture was warmed to 20° C., stirred for 15 h and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 7/3) to yield cis-6-bromo-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (130 mg, 0.38 mmol).

Workup

concentrationconcentrated in vacuo
customThe residue was chromatographed in silica gel column (Hex/EtOAc 7/3)

Sources & evidence

ORD record: ord-f8dcf54b2d614800924f2730166d6482
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795436B2

Reaction notes

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