Diethyl Ether → HCID 57786539, compound

HRID 253582Notes

Reaction equation

HRID 253582 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:1]=[CH:2][C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:4][CH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 57786513HCID 57786513, compound

Product 1

HCID 57786539HCID 57786539, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-hydroxy-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamate (1.7 g, 6.6 mmol) in CH2Cl2 (20 mL) was added Dess-Martin periodionane (3.4 g, 7.9 mmol). The reaction was stirred at r.t. for 1 h. Tlc showed the starting material had disappeared. The mixture was poured into Et2O (100 mL) and K2CO3 (5 g) was added. The organic phase was dried over Na2SO4 and concentrated. The residue was purified by chromatography to give (S)-tert-butyl 1-oxo-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamate (1.2 g, 71%). 1H NMR (CD3OD) δ 1.45 (s, 9H), 2.07 (m, 2H), 3.90 (m, 3H), 4.30 (b, 1H), 5.0 (b, 1H), 9.55 (s, 1H).

Workup

  1. additionwas added
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-9f13495967f348cc9cf2bf6b8d63f614
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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