Oxygen → HCID 11530891, compound

HRID 556022Notes

Reaction equation

HRID 556022 reaction equation
O=O.[C:3]([NH:11][C:12](=[CH:17][N:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>>[C:3]([NH:11][C@@H:12]([CH2:17][N:18]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 977OxygenHCID 66987425HCID 66987425, compound

Product 1

HCID 11530891HCID 11530891, compound

Procedure

With exclusion of oxygen and moisture, an ampule was charged with 100 mg of methyl 2-benzoylamino-3-diphenylaminoacrylate (0.255 mmol) and 1.9 mg (0.0026 mmol, 0.01 equivalent) of [(S,S)-Et-FerroTANE-Rh]BF4. After purging with argon, 5 ml of oxygen-free methanol were added. The ampule was sealed gas-tight and hydrogenated in an autoclave at 20 bar of hydrogen pressure for 24 h. The autoclave was decompressed and purged with nitrogen. The conversion of the hydrogenation was determined by HPLC. The enantioselectivity was determined by HPLC on chiral phase by the method described in Example 4. The [(R,R)-Et-FerroTANE-Rh]BF4 catalyst afforded the corresponding R derivative in the same yield and enantiomeric purity.

Workup

  1. customAfter purging with argon, 5 ml of oxygen-free methanol
  2. additionwere added
  3. customThe ampule was sealed gas-tight and hydrogenated in an autoclave at 20 bar of hydrogen pressure for 24 h
  4. custompurged with nitrogen
  5. customThe [(R,R)-Et-FerroTANE-Rh]BF4 catalyst afforded the corresponding R derivative in the
  6. customsame yield

Sources & evidence

ORD record
ord-bbfefc4a155f4ec0b8cfb8850c65b8b0
Source dataset
uspto-grants-2011_11
Patent number
US08053590B2

Reaction notes

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