Triethylamine → Carbamic acid, (2-methyl-1-propenyl)-, 1,1-dimethylethyl ester (9CI)

HRID 1612775Notes

Reaction equation

HRID 1612775 reaction equation
Cl.[CH2:2]([NH2:6])[C:3](=[CH2:5])[CH3:4].[C:7](=O)([O:13]C(C)(C)C)[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>ClCCl>[C:9]([O:8][C:7]([NH:6][CH:2]=[C:3]([CH3:4])[CH3:5])=[O:13])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 119537722-Methylallylamine hydrochloride

Product 1

HCID 14738325Carbamic acid, (2-methyl-1-propenyl)-, 1,1-dimethylethyl ester (9CI)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 13.44 g of methallylamine hydrochloride and 27.3 g of di-tert.-butyl carbonate in 250 ml of dichloromethane at 20° is treated with 25.2 g of triethylamine. The solution is stirred for 1 hour at 20° washed with water and the organic phase is dried and the solvent is removed to give a colourless oil. Flash-chromatography on silica-gel affords pure 3-(N-tert.-butoxycarbonylamino)-2-methyl-prop-2-ene as a colourless oil; 1H-NMR (CDCl3): δ (ppm)=4.83 (2H, m, 2×CH=C), 4.70-4.60 (1H, broad s, exch. D2O, NH), 3.67 (2H, s, CH2N), 1.73 (3H, s, CH3), 1.45 (9H, s, tBu).

Workup

  1. washwashed with water
  2. customthe organic phase is dried
  3. customthe solvent is removed
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-0ca1dbc0bea34512a567eb3e2bf96388
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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