Methanol → HCID 68548643, compound

HRID 2370279Notes

Reaction equation

HRID 2370279 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([CH2:22][CH2:23][CH2:24][OH:25])[CH2:13][CH2:12][CH:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:30].CO>C1COCC1>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([CH2:22][CH2:23][CH2:24][O:25][CH3:30])[CH2:13][CH2:12][CH:11]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 59226035HCID 59226035, compound

Product 1

HCID 68548643HCID 68548643, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 250 mg (0.65 mmol) of [4-(tert-butyl-dimethyl-silanyloxy)-1-(3-hydroxy-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (32) in 3 mL of THF was dropped into a suspension of 28.3 mg (0.71 mmol) of sodium hydride (60%) in 8 mL THF at 0° C. 120 μL (1.94 mmol) of iodomethane were added, and after stirring for 1 h at room temperature another 120 μL (1.94 mmol) of iodomethane were added. The reaction mixture was stirred for 14 h at room temperature, then 5 mL of methanol were added and the volatiles were removed in vacuo. Rt=2.32 min, 2.37 min (Method C). Detected mass: 402.3 (M+H+), 302.3 (M-Boc+H+).

Workup

  1. additionwere added
  2. customthe volatiles were removed in vacuo
  3. customRt=2.32 min, 2.37 min (Method C)

Sources & evidence

ORD record
ord-e26d00f823ff4d22ba2a7f9dad06abd3
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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