Triacetoxyperiodinane → tert-Butyl N-(3-formylcyclohexyl)carbamate

HRID 712036Notes

Reaction equation

HRID 712036 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:4]1)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22106830tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

Product 1

HCID 86717490tert-Butyl N-(3-formylcyclohexyl)carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [3-(hydroxymethyl)cyclohexyl]carbamate (0.51 g, 2.2 mmol) in methylene chloride (10 mL) at 0° C. was added Dess-Martin periodinane (1.1 g, 2.7 mmol). The mixture was stirred at room temperature for 2 h. The reaction was quenched with aq. 1N NaOH solution and extracted with methylene chloride. The combined organic layers were washed with water and then brine, dried over MgSO4, concentrated, and then purified on silica gel column (eluting with 20-50% EtOAc in hexanes) to give the desired product (0.3 g, 59%). LCMS calculated for C12H21NO3Na (M+Na)+: m/z=250.2. Found: 250.1.

Workup

  1. customThe reaction was quenched with aq. 1N NaOH solution
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel column (eluting with 20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c041ab20dc7d4b129b23dfde65ddf302
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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