Potassium Bromide → HCID 53956131, compound

HRID 1449535Notes

Reaction equation

HRID 1449535 reaction equation
[C:1]1([CH:7]2[NH:10][C:9](=[O:11])[CH:8]2[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].[K+].[Br-]>CO>[CH:1]1([CH:7]2[NH:10][C:9](=[O:11])[CH:8]2[OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 14807868HCID 14807868, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53956131HCID 53956131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

A suspension of 500 mg (3.06 mmol) of 4-phenyl-3-hydroxy-2-azetidinone VIa and 15 mg of Rh-C in 10 mL of methanol was heated at 90° C. under 800 psi in an autoclave. After 5 days, the hydrogen pressure was released and the catalyst filtered on celite. Evaporation of the solvent afforded a solid which was recrystallized in ethyl acetate to give 440 mg (85%) of VIIe as a white solid: White solid; mp 140°-140.5° C.; [α]D20 +65.1° (c 0.66, CH3OH); 1H NMR (250 MHz, MeOH-d4) δ 0.75-1.10 (m, 2H), 1.12-1.35 (m, 3H), 1.40-2.00 (m, 6H), 3.28 (dd, J=9.7, 4.6 Hz, 1H), 4.81 (d, J=4.6 Hz, 1H); 1H NMR (250 MHz, DMSO-d6) δ 0.75-1.00 (m, 2H), 1.10-1.35 (m, 3H), 1.37-1.55 (m, 1H), 1.58-1.85 (m, 5H), 3.10 (dd, J=9.6, 4.7 Hz, 1H), 4.67 (m, 1H), 5.87 (d, J=7.8 Hz, 1H), 8.21 (bs, 1H); 13C NMR (63 MHz, DMSO-d6) δ 25.08, 25.36, 26.07, 28.83, 29.17, 37.51, 59.04, 76.41, 170.21; IR (KBr) 3312, 3219, 2928, 1726 cm-1. Anal. Calcd for C9H15NO2 : C, 63.88, H, 8.93, N, 8.28. Found: C, 63.70, H, 9.00, N, 8.06.

Workup

  1. filtrationthe catalyst filtered on celite
  2. customEvaporation of the solvent
  3. customafforded a solid which
  4. customwas recrystallized in ethyl acetate
  5. customto give 440 mg (85%) of VIIe as a white solid

Sources & evidence

ORD record
ord-fb948f8370cb4ab69643bf21676fea3f
Source dataset
uspto-grants-1997_02
Patent number
US05599820

Reaction notes

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