Triethylamine → Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester

HRID 1790609Notes

Reaction equation

HRID 1790609 reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:12]([NH:15][CH:16]([CH3:21])[CH2:17][CH2:18][CH:19]=[CH2:20])[CH:13]=[CH2:14].C(N(CC)CC)C>C(Cl)Cl>[CH2:4]([O:3][C:1](=[O:2])[N:15]([CH2:12][CH:13]=[CH2:14])[CH:16]([CH3:21])[CH2:17][CH2:18][CH:19]=[CH2:20])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11788335Allyl-(1-methyl-pent-4-enyl)-amine

Product 1

HCID 11608774Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl esterYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Carbobenzyloxy chloride (9.56 g, 8 ml) was added dropwise to a stirred solution of allyl-(1-methyl-pent-4-enyl)-amine (7 g, 50 mmol), triethylamine (5.5 g, 8.0 ml, 57.5 mmol) in CH2Cl2 (100 ml) at 0 C. The reaction mixture was warmed to RT, then was stirred for 2 h. The reaction mixture was diluted with CH2Cl2 (100 ml), then was extracted with water, then brine. The combined organics were dried with MgSO4, filtered, concentrated in vacuo by rotary evaporation, then was chromatographed (silica gel, 4% EtOAc/hexanes) to give the title compound (8.9 g, 65% yield): Liquid Chromatgraphy/Electrospray mass spec: M+H+=274.2.

Workup

  1. extractionwas extracted with water
  2. dry with materialThe combined organics were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo by rotary evaporation
  5. customwas chromatographed (silica gel, 4% EtOAc/hexanes)

Sources & evidence

ORD record
ord-13dcccafe5e44af2930e2ec876392e13
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Reaction notes

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