5-Fluoro-2-nitrophenol → HCID 69669165, compound

HRID 450577Notes

Reaction equation

HRID 450577 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[F:17][C:18]1[CH:19]=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[C:22]([OH:24])[CH:23]=1.O[CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[C:22]([CH:23]=1)[O:24][CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 69669165HCID 69669165, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Di-tert-butyl azodicarboxylate (5.27 g, 23.0 mmol) in DCM (10 mL) was added into a solution of 5-fluoro-2-nitrophenol (10 g, 63.7 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (4.22 g, 21.0 mmol) and triphenyl phosphine (6.0 g, 23.0 mmol) in anhydrous DCM (40 mL) at 0° C. The solution was allowed to warm to ambient temperature overnight, concentrated in vacuo and the crude product triturated with n-pentane/diethyl ether (×2) to remove the triphenyl phosphine oxide by-product. The sample was purified by dry flash chromatography (1:10→1:1 EtOAc/iso-hexane) to yield yellow oil (2.6 g, 40%).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe crude product triturated with n-pentane/diethyl ether (×2)
  3. customto remove the triphenyl phosphine oxide by-product
  4. customThe sample was purified
  5. dry with materialby dry flash chromatography (1:10→1:1 EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-3e64d18be3c74ed28f6b06159d7f215c
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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