Benzoic Acid → HCID 59455633, compound

HRID 73525Notes

Reaction equation

HRID 73525 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[Si:36]([O:43][C@@H:44]1[CH2:49][C@@H:48]([OH:50])[CH2:47][N:46]([C:51]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:52])[CH2:45]1)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].[C:61](O)(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C1COCC1>[C:61]([O:50][C@H:48]1[CH2:49][C@@H:44]([O:43][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:45][N:46]([C:51]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:52])[CH2:47]1)(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 58386793HCID 58386793, compound

Product 1

HCID 59455633HCID 59455633, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring 0° C. solution of triphenylphosphine (1.2 equiv) in 23 mL of THF was added di-tert-butyl azodicarboxylate (1.2 equiv). The mixture was stirred at 0° C. for 10 minutes. Then a solution of (3R,5R)-benzyl 3-(tert-butyldimethylsilyloxy)-5-hydroxypiperidine-1-carboxylate (1.0 equiv) in 11 mL of THF was added and stirred for 20 minutes at 0° C. Benzoic acid (1.2 equiv) was then added and the reaction mixture was allowed to slowly warm to rt. After 16 hours the reaction mixture was concentrated in vacuo then diluted with EtOAc and washed with water then brine. The organic layer was dried with Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:8) to yield (3S,5R)-benzyl 3-(benzoyloxy)-5-(tert-butyl-dimethylsilyloxy)piperidine-1-carboxylate (77%). LC/MS (m/z): 470.2 (MH+), HPLC Rt=6.05 min.

Workup

  1. stirringstirred for 20 minutes at 0° C
  2. temperatureto slowly warm to rt
  3. concentrationAfter 16 hours the reaction mixture was concentrated in vacuo
  4. additionthen diluted with EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=1:8)

Sources & evidence

ORD record
ord-420719bcf88248a7bf2402f20cf883ee
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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