Triacetoxyperiodinane → (S)-Tert-butyl 1-cyclohexyl-3-oxopropan-2-ylcarbamate

HRID 2355368Notes

Reaction equation

HRID 2355368 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][OH:10])[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>ClCCCl.CCOCC>[CH:1]1([CH2:7][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11043405(S)-(-)-2-(tert-Butoxycarbonylamino)-3-cyclohexyl-1-propanol

Product 1

HCID 10848617(S)-Tert-butyl 1-cyclohexyl-3-oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of tert-butyl (S)-3-cyclohexyl-1-hydroxypropan-2-ylcarbamate (0.23 g, 0.9 mmol) in 1,2-dichloroethane (5 mL), was added Dess-Martin periodinane (0.49 g, 1.34 mmol). The resulting mixture was heated in a CEM microwave synthesizer at 70° C. for 3 min, diluted with ether (100 mL), and washed with 1 N NaOH (2×10 mL). The ether layer was dried over Na2SO4, and the solvent was removed in vacuo to give (S)-tert-butyl 1-cyclohexyl-3-oxopropan-2-ylcarbamate as an oil. MS ESI+ve m/z 256 (M+1).

Workup

  1. washwashed with 1 N NaOH (2×10 mL)
  2. dry with materialThe ether layer was dried over Na2SO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-72d7feae9da849008aea25a5e3bb2f04
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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