Potassium Carbonate → 4,4'-Bipiperidine, 1-boc protected

HRID 419409Notes

Reaction equation

HRID 419409 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[CH3:13][C:14]([O:17][C:18](ON=C(C1C=CC=CC=1)C#N)=[O:19])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(Cl)(Cl)Cl>[N:1]1([C:18]([O:17][C:14]([CH3:16])([CH3:15])[CH3:13])=[O:19])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 7360504,4'-Bipiperidine

Product 1

HCID 117475994,4'-Bipiperidine, 1-boc protectedYield 45.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 4,4′-bipiperidine (5.48 g, 32.6 mmol) in THF (160 mL) and CHCl3 (160 mL) was added BOC-On (4.01 g) in THF (90 mL) dropwise over a 8 h period. The reaction was then concentrated and purified by flash chromatography. The residue was taken up in 1M KHSO4 (250 mL) and washed with diethyl ether (three times). K2CO3 (38.0 g, 275 mmol) was added to the aqueous layer which was subsequently extracted with CHCl3 (3×), dried (MgSO4) and concentrated to provide the title compound of step A (1.98 g, 7.40 mmol, 45%). 1H NMR (400 MHz, CDCl3) δ ppm 1.06-1.18 (m, 5H), 1.42 (s, 9H), 1.58-1.69 (m, 6H), 2.50-2.61 (m, 4H), 3.06 (d, J=12.1 Hz, 2H), 4.08 (br. s., 2H).

Workup

  1. concentrationThe reaction was then concentrated
  2. custompurified by flash chromatography
  3. washwashed with diethyl ether (three times)
  4. extractionwas subsequently extracted with CHCl3 (3×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31dec6755c584370813042c4481a5663
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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