Triacetoxyperiodinane → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

HRID 1398381Notes

Reaction equation

HRID 1398381 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]([CH3:7])[CH3:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:6][CH:5]([CH3:7])[CH2:4][C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 7018766Boc-L-leucinol

Product 1

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate (2 g, 9.20 mmol) in DCM (30 mL) was added Dess-Martin Periodinane (5.86 g, 13.81 mmol) at 0° C. The reaction mixture was allowed to stir at RT for 16 h. The reaction mixture was quenched with NaHCO3, diluted with water and extracted in ethyl acetate. Organic layer was dried over Na2SO4 and concentrated which afforded (S)-tert-butyl (4-methyl-1-oxopentan-2-yl)carbamate as colorless oil (1.4 g, 6.50 mmol, 71% crude yield). The material was carried on without further purification. 1H NMR (300 MHz, DMSO-d6): δ 0.8-0.96 (m, 6H), 1.31-1.49 (m, 11H), 1.57-1.66 (m, 1H), 3.81-3.89 (m, 1H). 7.27 (d, 1H), 9.43 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with NaHCO3
  2. additiondiluted with water
  3. extractionextracted in ethyl acetate
  4. dry with materialOrganic layer was dried over Na2SO4
  5. concentrationconcentrated which

Sources & evidence

ORD record
ord-2bb1d37db1484e62899ba356bdfcfb3f
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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