HCID 10936090, compound → HCID 11819439, compound

HRID 324707Notes

Reaction equation

HRID 324707 reaction equation
C([Si](C(C)C)(C(C)C)[O:5][C@@H:6]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:8][C:7]1=[O:16])(C)C.[H][H]>CO>[CH:10]1([C@@H:9]2[NH:8][C:7](=[O:16])[C@@H:6]2[OH:5])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 10936090HCID 10936090, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11819439HCID 11819439, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 500 mg (3.06 mmol) of 4-phenyl-3-hydroxy-2-azetidinone 1a 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 filtrated on celite. Evaporation of the solvent afforded a solid which was recrystallized in ethyl acetate to give 440 mg (85%) of 3e 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.

Workup

  1. filtrationthe catalyst filtrated on celite
  2. customEvaporation of the solvent
  3. customafforded a solid which
  4. customwas recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-381d3a4920c542eda1ea2a500ce4c077
Source dataset
uspto-grants-2001_04
Patent number
US06218553B1

Reaction notes

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