Methyl iodide → Tert-butyl (cyclopropylmethyl)(methyl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:16]>CN(C=O)C>[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:8][CH:9]1[CH2:10][CH2:11]1)[CH3:16])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl(cyclopropylmethyl)carbamate (4 g, 23.4 mmol) in DMF (35 mL) was added to a suspension of NaH (60% suspension in mineral oil) (0.58 g, 25.7 mmol) in DMF (5 mL) at 0-5° C., to it was added Iodomethane (2.5 mL, 40 mmol) and stirring was continued at 25° C. for 16 h. Reaction mixture was quenched with cold water, extracted with ethyl acetate (3×50 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude, which was purified by flash chromatography (Biotage, Column: silica gel 12 g pack size, solid load, Mobile Phase: EtOAc in n-Hexane: 0 to 5% as eluent) to afford tert-butyl(cyclopropylmethyl)(methyl)carbamate (Int-37) as pale yellow oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.0-2.9 (2H, d), 2.85 (3H, s), 1.4 (9H, s), 0.9-0.7 (1H, bs), 0.5-0.3 (2H, m), 0.2-0.05 (2H, m).
Workup
- customReaction mixture
- customwas quenched with cold water
- extractionextracted with ethyl acetate (3×50 mL)
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
- customto afford the crude, which
- customwas purified by flash chromatography (Biotage, Column: silica gel 12 g pack size, solid load, Mobile Phase: EtOAc in n-Hexane: 0 to 5% as eluent)
Sources & evidence
- ORD record
- ord-93667915d9cd40f1a1b339dcf95fed1b
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09402833B2
Reaction notes
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