Chlorotrimethylsilane → HCID 57535331, compound

HRID 1455578Notes

Reaction equation

HRID 1455578 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([CH2:15][CH3:16])[CH:9]([OH:14])[CH2:10][N+:11]([O-:13])=[O:12])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:25][Si:26](Cl)([CH3:28])[CH3:27]>ClCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([CH2:15][CH3:16])[CH:9]([O:14][Si:26]([CH3:28])([CH3:27])[CH3:25])[CH2:10][N+:11]([O-:13])=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 57535338HCID 57535338, compound

Product 1

HCID 57535331HCID 57535331, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (1-ethyl-2-hydroxy-3-nitro-propyl)-carbamic acid tert-butyl ester (1.83 g, 7.37 mmol) and triethylamine (1.49 g, 14.75 mmol) in dry dichloromethane (25 mL) under N2 is added trimethylsilyl chloride (1.20 g, 11.05 mmol). The mixture is stirred at room temperature for 24 h, then diluted with 40 mL of dichloromethane and washed with water (40 mL). The organic layer is dried over magnesium sulfate and concentrated in vacuum. The residue is purified over 110 g silica gel, eluted with ethyl acetate: heptane (1:4) to afford (1-ethyl-3-nitro-2-trimethylsilanyloxy-propyl)-carbamic acid tert-butyl ester (1.505 g, 86%) as an oil.

Workup

  1. washwashed with water (40 mL)
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated in vacuum
  4. customThe residue is purified over 110 g silica gel
  5. washeluted with ethyl acetate: heptane (1:4)

Sources & evidence

ORD record
ord-f81353dbc15f4ebda2ad52776891ede7
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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