Butanenitrile, 4-chloro-3-hydroxy- → HCID 58180980, compound

HRID 1772814Notes

Reaction equation

HRID 1772814 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:16][CH:17]([OH:21])[CH2:18][C:19]#[N:20].C(=O)(O)[O-].[Na+]>C(O)C>[C:19]([CH2:18][CH:17]([OH:21])[CH2:16][N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]1)#[N:20]

Participants

5

Reactant 3

HCID 92736Butanenitrile, 4-chloro-3-hydroxy-HCID 516892Sodium BicarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 58180980HCID 58180980, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 1,4-diazepane-1-carboxylate (4.65 g, 23.2 mmol) and 4-chloro-3-hydroxybutanenitrile (2.0 g, 17 mmol) in ethanol (40 mL) was added sodium bicarbonate (2.1 g, 25 mmol). The mixture was stirred at 90° C. for 19 hours. After cooling to room temperature, ethanol was evaporated. The remaining mixture was diluted with ethyl acetate and washed with water and brine. The organic was dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel column (0% to 10% methanol/DCM) to give the desired product as yellow oil (3.2 g, 68%). LCMS calculated for C14H26N3O3(M+H)+: m/z=284.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. customethanol was evaporated
  3. additionThe remaining mixture was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (0% to 10% methanol/DCM)

Sources & evidence

ORD record
ord-2c97e9e938414df982100744aad5c9c3
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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