Imidazole → HCID 12944336, compound

HRID 321946Notes

Reaction equation

HRID 321946 reaction equation
[I:1]I.[Si:3]([N:10]1[C@@H:13]([CH2:14]O)[CH2:12][C:11]1=[O:16])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1>CC#N>[Si:3]([N:10]1[C@@H:13]([CH2:14][I:1])[CH2:12][C:11]1=[O:16])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 11074788HCID 11074788, compound

Product 1

HCID 12944336HCID 12944336, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodine (4.25 g, 16.7 mmol) was added to a solution of 1-(tert-butyldimethylsilyl)-4(R)-(hydroxymethyl)azetidin-2-one (2.25 g, 10.47 mmol), Ph3P (5.48 g, 20.93 mmol) and imidazole (1.64 g, 24.07 mmol) in MeCN (100 mL) at 0°. After stirring at room temperature for four days, the mixture was concentrated and suspended in EtOAc-hexane (1:1). The suspension was filtered through a silica gel pad and washed with EtOAc-hexane (1:1). Concentration of the filtrate and purification by flash chromatography (SiO2, 10% EtOAc-hexane) afforded pure 1-(tert-butyldimethylsilyl)-4(R)-(iodomethyl)azetidin-2-one as a white solid (2.73 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ 3.72-3.66 (m, 1H), 3.50 (ddd, J=9.8, 3.2, 0.6 Hz, 1H), 3.21 (ddd, J=15.6, 5.4, 0.6 Hz, 1H), 3.11 (dd, J=9.8, 9.8 Hz, 1H), 2.76 (dd, J=15.6, 2.5 Hz, 1H), 0.96 (s, 9H), 0.27 (s, 3H), 0.22 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated
  2. filtrationThe suspension was filtered through a silica gel pad
  3. washwashed with EtOAc-hexane (1:1)
  4. customConcentration of the filtrate and purification by flash chromatography (SiO2, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-ce0adec67e06424a8a8d5621490e0421
Source dataset
uspto-grants-2001_04
Patent number
US06211170B1

Reaction notes

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