1,3-Dibromobutane → HCID 21931679, compound

HRID 1244000Notes

Reaction equation

HRID 1244000 reaction equation
C(NCC)C.[Li]CCCC.[C:11]([Si:15]([CH3:28])([CH3:27])[N:16]1[CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][C:17]1=[O:26])([CH3:14])([CH3:13])[CH3:12].Br[CH2:30][CH2:31][CH:32]([Br:34])[CH3:33].[NH4+].[Cl-]>C1COCC1>[Br:34][CH:32]([CH3:33])[CH2:31][CH2:30][CH:18]1[CH:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:16]([Si:15]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:28])[CH3:27])[C:17]1=[O:26]

Participants

7

Reactant 5

HCID 78891,3-DibromobutaneHCID 8021DiethylamineHCID 25517Ammonium ChlorideHCID 13583686HCID 13583686, compoundHCID 178418339Butyllithium

Product 1

HCID 21931679HCID 21931679, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To diethylamine (4.32 g, 59.0 mmol) in 22 mL of THF at 0° C. was added nBuLi (2.5 M in hexanes; 50.6 mmol, 20.2 mL). After 15 minutes the solution was added via cannula to a −50° C. solution of 1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidin-2-one (11.0 g, 42.2 mmol) in 110 mL of THF. After stirring for 20 minutes, 1,3-dibromobutane was added and the solution was stirred for 1 hour. Saturated aqueous NH4Cl was added and the mixture was warmed to room temperature and extracted once with ether. The extract was dried with MgSO4, concentrated and chromatographed (9:1 hexanes/EtOAc) to give 11.4 g (68%) of the title compound as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ comp, 10H), 4.21 (d, J=2.5 Hz, 1H), 4.16 (d, J=2.5 Hz, 1H), 4.08 (m, 1H), 3.02 (m, 1H), 1.80–2.10 (comp, 4H), 1.67 (d, J=6.6 Hz, 3H), 0.90 (s, 9H), 0.18 (s, 3H), −0.22 (s, 3H); Mass spectrum m/e calcd for M+H=396.2. Found 396.0 (base), 316.

Workup

  1. stirringthe solution was stirred for 1 hour
  2. extractionextracted once with ether
  3. dry with materialThe extract was dried with MgSO4
  4. concentrationconcentrated
  5. customchromatographed (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-4802a4ab2db449ccb36459110033330d
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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