2-Bromopropane → HCID 57986056, compound

HRID 1869221Notes

Reaction equation

HRID 1869221 reaction equation
[O:1]=[C:2]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH:4]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[NH:3]1.[H-].[Na+].Br[CH:28]([CH3:30])[CH3:29]>CN(C=O)C>[O:1]=[C:2]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH:4]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[N:3]1[CH:28]([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 57986039HCID 57986039, compound

Product 1

HCID 57986056HCID 57986056, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In a dry 100 mL 3-necked flask, add 1,1-dimethylethyl 1-oxo-3-(4-chlorophenyl) -2,7-diazaspiro[3.5]nonane-7-carboxylate (7.0 g) and dry DMF (50 mL) and cool to ˜2 C. Add portionwise sodium hydride in 60% oil dispersion (1.10 g) keeping temperature at 2-5 C. After 5 min., add portionwise 2-bromopropane (2.6 mL) keeping temperature 3 to 8° C. Warm mixture to 50° C. After 4.5 h, cool to ˜20° C. and add ice water (400 mL). Extract with EtOAc (2×499 mL). Extract EtOAc with brine (50 mL). Concentrate the dried (MgSO4) EtOAc in vacuo to give the title compound as an amber oil (8.80 g). Add EtOAc:hexane (1:2, 20 mL) and keep overnight at RT to give the title compound as a yellow solid (5.75 g).

Workup

  1. temperaturecool to ˜2 C
  2. customtemperature 3 to 8° C
  3. waitAfter 4.5 h
  4. temperaturecool to ˜20° C.
  5. extractionExtract with EtOAc (2×499 mL)
  6. concentrationConcentrate the
  7. dry with materialdried (MgSO4) EtOAc in vacuo

Sources & evidence

ORD record
ord-6639550cf61d44c68b0a4bca29e34fa6
Source dataset
uspto-grants-2009_12
Patent number
US07638526B2

Reaction notes

Loading…