N-bromobutanimide → 5-bromo-6-(4-fluorophenyl)-7-methyl-2,3-dihydro-1H-pyrrolizine

HRID 586622Notes

Reaction equation

HRID 586622 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:15]([CH3:16])=[C:14]3[N:10]([CH2:11][CH2:12][CH2:13]3)[CH:9]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.C(OC(C)C)(C)C.CCCCCC>C1COCC1>[Br:17][C:9]1[N:10]2[C:14](=[C:15]([CH3:16])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:13][CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 21881879Diisopropylether hexaneHCID 223356466-(4-fluorophenyl)-7-methyl-2,3-dihydro-1H-pyrrolizine

Product 1

HCID 223356085-bromo-6-(4-fluorophenyl)-7-methyl-2,3-dihydro-1H-pyrrolizineYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 6-(4-fluorophenyl)-7-methyl-2,3-dihydro-1H-pyrrolizine (9.0 g, 42 mmol) in abs. THF (50 ml) is cooled to −15° C. N-Bromosuccinimide (3.46 g, 19.4 mmol) is added in portions; the mixture is stirred until no more starting material is detectable (TLC SiO2, diisopropyl ether-hexane 2:1). The black-purple-coloured reaction mixture is chromatographed on a column (20 cm×3 cm) packed with Al2O3 (ICI, for dry packing). The column is subsequently washed with n-hexane (80 ml), and the filtrates are concentrated. 3.55 g (28.9%) of a black-brown oil are obtained, which rapidly decomposes.

Workup

  1. customThe black-purple-coloured reaction mixture is chromatographed on a column (20 cm×3 cm)
  2. washThe column is subsequently washed with n-hexane (80 ml)
  3. concentrationthe filtrates are concentrated

Sources & evidence

ORD record
ord-fb82db299d9e4384a13dda164deab877
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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