Triethylamine → (1,1-Dimethyl-4-nitro-but-3-enyl)-carbamic acid tert-butyl ester

HRID 1244078Notes

Reaction equation

HRID 1244078 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]([CH3:17])([CH3:16])[CH2:9][CH:10](O)[CH2:11][N+:12]([O-:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]([CH3:17])([CH3:16])[CH2:9][CH:10]=[CH:11][N+:12]([O-:14])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86587888(3-Hydroxy-1,1-dimethyl-4-nitro-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 73740413(1,1-Dimethyl-4-nitro-but-3-enyl)-carbamic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To (3-Hydroxy-1,1-dimethyl-4-nitro-butyl)-carbamic acid tert-butyl ester (2.00 g, 7.6 mmol) and triethylamine (2.73 g, 27.0 mmol) in 50 mL CH2Cl2 at −10° C. was added dropwise over 5 min. methanesulfonyl chloride. The mixture was warmed to rt for 1 h, and then was diluted with water and extracted with CH2Cl2 (3×30 mL). The extracts were washed sequentially with 1% HCl, water and brine and were dried over MgSO4 and concentrated. Silica gel chromatography (10:1 hexane/EtOAc) gave 1.07 g (60%) of a colorless oil: 1H NMR (300 MHz, CD3OD) d 7.1–7.4 (comp, 2H), 2.72 (d, 2H, J 7.5 Hz), 1.46(s, 9H), 1.31 (s, 6H).

Workup

  1. extractionextracted with CH2Cl2 (3×30 mL)
  2. washThe extracts were washed sequentially with 1% HCl, water and brine
  3. dry with materialwere dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a4ca7e773ff84863a89f26724b66e89d
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…