Methyl iodide → HCID 57679159, compound

HRID 492150Notes

Reaction equation

HRID 492150 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1([CH2:18][CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].IC.[CH3:27][Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:8][C:9]1([CH2:18][CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)[CH3:27])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 57679134tert-butyl [1-(1,3-dioxolan-2-ylmethyl)-2,3-dihydro-1H-inden-1-yl]methylcarbamate

Product 1

HCID 57679159HCID 57679159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl[1-(1,3-dioxolan-2-ylmethyl)-2,3-dihydro-1H-inden-1-yl]methylcarbamate (13.50 g, 38.9 mmole) in THF was cooled to 0° C. To this was added iodomethane (7.27 ml, 117 mmole) followed by 1M NaHMDS in THF (58 ml, 58 mmole). The reaction was then warmed to room temperature and stirred until no U16370/185/2 remained by TLC. The THF was evaporated and the residue dissolved in Et2O. The ether was washed with water and evaporated to afford 14.33 g of tert-butyl[1-(1,3-dioxolan-2-ylmethyl)-2,3-dihydro-1H-inden-1-yl]methyl(methyl)carbamate as a crude oil, which was used, with no further purification.

Workup

  1. customThe THF was evaporated
  2. dissolutionthe residue dissolved in Et2O
  3. washThe ether was washed with water
  4. customevaporated

Sources & evidence

ORD record
ord-8b74e1d4819b4bf0975073885031e435
Source dataset
uspto-grants-2009_05
Patent number
US07531661B2

Reaction notes

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