Triacetoxyperiodinane → tert-Butyl 4-oxopiperidine-1-carboxylate

HRID 712446Notes

Reaction equation

HRID 712446 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (58.50 g) in CH2Cl2 was added Dess-Martin agent (174.10 g) in portions at 0° C. The reaction mixture was stirred for 2 h at room temperature, and quenched with water. The resulted mixture was extracted with CH2Cl2 (200 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 3:1 (v/v) PE/EA) to give the title compound as a white solid (52.00 g, 90.00%), HPLC: 97.50%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 200.5 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.42 (s, 9H), 2.78 (m, J=6.4 Hz, 2H), 3.56 (t, J=6.4 Hz, 2H), 4.28 (t, J=6.4 Hz, 2H), 4.50 (s, 2H) ppm.

Workup

  1. customquenched with water
  2. extractionThe resulted mixture was extracted with CH2Cl2 (200 mL×3)
  3. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was chromatographed with a silica gel column (eluting agent: 3:1 (v/v) PE/EA)

Sources & evidence

ORD record
ord-187876b0ac3c4a40a1331db64207ec64
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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