2-Chloroethyl chloroformate → 6-Nitro-3-azabicyclo[3.1.0]hexane hydrochloride

HRID 2079776Notes

Reaction equation

HRID 2079776 reaction equation
C([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[N+:14]([O-:16])=[O:15])[CH2:9]1)C1C=CC=CC=1.[Cl:17]CCOC(Cl)=O>ClCCCl>[ClH:17].[N+:14]([CH:11]1[CH:12]2[CH:10]1[CH2:9][NH:8][CH2:13]2)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformate2×HCID 215851823-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

Product 1

HCID 213110856-Nitro-3-azabicyclo[3.1.0]hexane hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 3-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane (2.47 g, 11.3 mmol) in 1,2-dichloroethane (5 ml) was added chloroethylchloroformate (1.83 ml, 16.9 mmol) at 0° C. The reaction mixture was heated to 55° C. for 4 h. Further chloroethylchloroformate (0.5 ml) was added and heating continued for 2 h. The reaction mixture was evaporated to dryness. MeOH (15 ml) was added and the reaction mixture was heated at 65° C. for 3 h. Conc. HCl (1 ml) was added and the reaction stirred at r.t. for 2 h. A grey precipitate had formed, this was isolated by filtration and washed with Et2O. The title compound was obtained as a grey powder (464 mg, 25%). 1H NMR (300 MHz, d6-DMSO) δ: 2.90 (2H, s), 3.3-3.6 (4H, m), 4.75 (1H, s), 9.50 (2H, br s).

Workup

  1. temperatureheating
  2. customThe reaction mixture was evaporated to dryness
  3. additionMeOH (15 ml) was added
  4. temperaturethe reaction mixture was heated at 65° C. for 3 h
  5. additionConc. HCl (1 ml) was added
  6. customA grey precipitate had formed
  7. customthis was isolated by filtration
  8. washwashed with Et2O

Sources & evidence

ORD record
ord-e3da7f2df9674242929812284f5b45fa
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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