4-Nitrobenzoic Acid → (1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate

HRID 539078Notes

Reaction equation

HRID 539078 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)(=O)C>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]2[NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:15])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10013520(1S,2S)-trans-N-Boc-2-Aminocyclohexanol

Product 1

HCID 68089026(1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoateYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (1S,2S)-2-hydroxycyclohexylcarbamate (1.30 g, 6.04 mmol), 4-nitrobenzoic acid (1.11 g, 6.64 mmol), triphenylphosphine (1.74 g, 6.64 mmol) in THF (30 mL) was added diethylazo dicarboxylate (1.05 ml, 6.64 mmol) and the resulting solution was stirred at ambient temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried and concentrated to give an orange oil that was purified by column chromatography (hexanes/ethyl acetate, 8:1) to give (1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate (1.95 g, 89%).

Workup

  1. washwashed with brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto give an orange oil that
  5. customwas purified by column chromatography (hexanes/ethyl acetate, 8:1)

Sources & evidence

ORD record
ord-2434db54abe248be933c2066c0db3825
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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