4-Nitrobenzoic Acid → HCID 86742923, compound

HRID 620326Notes

Reaction equation

HRID 620326 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C@@H:6]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[OH:17])[CH2:7][N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:39]([C:42]1[CH:50]=[CH:49][C:45]([C:46](O)=[O:47])=[CH:44][CH:43]=1)([O-:41])=[O:40].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N+:39]([C:42]1[CH:43]=[CH:44][C:45]([C:46]([O:17][C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]2[C@@H:6]([CH2:7][N+:8]([O-:10])=[O:9])[C:5]2[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:47])=[CH:49][CH:50]=1)([O-:41])=[O:40]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54286267HCID 54286267, compound

Product 1

HCID 86742923HCID 86742923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9.1 g (32.1 mmol) of rac-(1S*)-cis-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanol, 16.8 g (64.2 mmol) of triphenylphosphine and 10.8 g (64.2 mmol) of p-nitrobenzoic acid are dissolved in 180 ml of tetrahydrofuran. To this solution is added dropwise with 30 minutes a solution of 11.3 g (64.2 mmol) of diethyl azodicarboxylate in 80 ml of tetrahydrofuran and the mixture is subsequently stirred at room temperature for 5 hours. After distilling off the solvent the residue obtained is chromatographed on a 30-fold amount of silica gel while eluting with toluene/hexane (1:2). By recrystallization of the product obtained from methylene chloride/hexane there is obtained rac-(1R*)-trans-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexyl p-nitrobenzoate in the form of colourless crystals of m.p. 146°-148°.

Workup

  1. distillationAfter distilling off the solvent the residue
  2. customobtained
  3. customis chromatographed on a 30-fold amount of silica gel
  4. washwhile eluting with toluene/hexane (1:2)
  5. customBy recrystallization of the product
  6. customobtained from methylene chloride/hexane there

Sources & evidence

ORD record
ord-1c71e71d9bea49a98db7f80cd01c9950
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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