Iodine → Tert-butyl 3-(3,4-difluorophenyl)-3-hydroxypyrrolidine-1-carboxylate

HRID 575973Notes

Reaction equation

HRID 575973 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([F:9])[CH:3]=1.[Mg].II.[C:13]([N:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>O1CCCC1>[F:9][C:4]1[CH:3]=[C:2]([C:22]2([OH:25])[CH2:23][CH2:24][N:20]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:21]2)[CH:7]=[CH:6][C:5]=1[F:8]

Participants

6

Reactant 4

HCID 807IodineHCID 676754-Bromo-1,2-difluorobenzeneHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 5462224Magnesium

Product 1

HCID 67405004Tert-butyl 3-(3,4-difluorophenyl)-3-hydroxypyrrolidine-1-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation according to Preparation 1. 1-Bromo-3,4-difluorobenzene (5 g, 25.9 mmol) in dry tetrahydrofuran (100 ml), magnesium turnings (0.62 g, 25.9 mmol) and one crystal of iodine. 1-N-boc-3-pyrrolidone (4.79 g, 25.9 mmol) in dry tetrahydrofuran (50 ml). The crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1) gave the title compound (3.3 g, 43%). MS m/z (rel. intensity, 70 eV) 243 (33), 198 (45), 141 (39), 127 (44), 57 (bp).

Workup

  1. customPreparation
  2. customaccording to Preparation 1
  3. customThe crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1)

Sources & evidence

ORD record
ord-da9178dd1be94698a1095fd287f76b5a
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

Loading…