4-Nitrobenzoic Acid → HCID 67823507, compound

HRID 1109760Notes

Reaction equation

HRID 1109760 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([N:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][C@@H:21]1[CH3:27])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[N+:28]([C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1)([O-:30])=[O:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:13]([N:20]1[CH2:25][CH2:24][C@@H:23]([O:26][C:35](=[O:36])[C:34]2[CH:33]=[CH:32][C:31]([N+:28]([O-:30])=[O:29])=[CH:39][CH:38]=2)[CH2:22][C@@H:21]1[CH3:27])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 450974401-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4S)-(9CI)

Product 1

HCID 67823507HCID 67823507, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

With stirring, a solution of 2 ml (0.012 mol) of diethyl azodicarboxylate (93%) in 10 ml of toluene is added dropwise at 5°-10° C. to a suspension of 2.15 g (0.01 mol) of cis-N-BOC-2-methyl-4-hydroxypiperidine (cf. Example 1b), 2.0 g (0.012 mol) of 4-nitrobenzoic acid and 3.15 g (0.012 mol) of triphenylphosphine in 30 ml of toluene. The reaction mixture is further stirred for 15 hours at room temperature and then filtered to remove precipitated diethyl hydrazinedicarboxylate. The filtrate is then concentrated under vacuum and the oily residue is purified by flash chromatography over silica gel using ethyl acetate:hexane (1:5). Concentration of the fractions containing the product gives the title compound as a crystalline residue which melts at 106°-108° C.

Workup

  1. stirringThe reaction mixture is further stirred for 15 hours at room temperature
  2. filtrationfiltered
  3. customto remove
  4. customprecipitated diethyl hydrazinedicarboxylate
  5. concentrationThe filtrate is then concentrated under vacuum
  6. customthe oily residue is purified by flash chromatography over silica gel
  7. additionConcentration of the fractions containing the product

Sources & evidence

ORD record
ord-1927b72fe78845a6baa4a5f9a96096fc
Source dataset
uspto-grants-1994_06
Patent number
US05322852

Reaction notes

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