Triacetoxyperiodinane → (+/-)-[2-[1,4']Bipiperidinyl-1'-yl-2-oxo-1-(4-oxo-piperidin-1-ylmethyl)-ethyl]-carbamic acid tert-butyl ester

HRID 2250203Notes

Reaction equation

HRID 2250203 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13](=[O:38])[CH:14]([N:23](C(OC(C)(C)C)=O)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:27]([O:26][C:24](=[O:25])[NH:23][CH:14]([CH2:15][N:16]1[CH2:17][CH2:18][C:19](=[O:22])[CH2:20][CH2:21]1)[C:13]([N:10]1[CH2:11][CH2:12][CH:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9]1)=[O:38])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 211020511-[1,4']Bipiperidinyl-1'-yl-2-(di-tert-butoxycarbonylamino)-3-(4-hydroxy-piperidin-1-yl)-propan-1-one

Product 1

HCID 58864249(+/-)-[2-[1,4']Bipiperidinyl-1'-yl-2-oxo-1-(4-oxo-piperidin-1-ylmethyl)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1,4′]bipiperidinyl-1′-yl-2-(di-tert-butoxycarbonylamino)-3-(4-hydroxy-piperidin-1-yl)-propan-1-one (200 mg, 0.37 mmol) in methylene chloride (4 mL) was added Dess-Martin periodinane (316 mg, 2 equiv) in two portions. After 1 h, the reaction was quenched by the addition of saturated sodium bicarbonate, and extracted into methylene chloride (3×). The combined organic phases were washed with brine, dried over magnesium sulfate, and concentrated to give 187 mg (94%) which was used without purification. Mass spec.: 437.63 (MH)+.

Workup

  1. customthe reaction was quenched by the addition of saturated sodium bicarbonate
  2. extractionextracted into methylene chloride (3×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give 187 mg (94%) which
  7. customwas used without purification

Sources & evidence

ORD record
ord-3c21db0633f2472181630c1b4c9ef24f
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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