Diisopropylethylamine → HCID 57743052, compound

HRID 1924330Notes

Reaction equation

HRID 1924330 reaction equation
O[CH:2]1O[C:5](=[O:7])[CH2:4][CH:3]1[CH2:8][CH2:9][CH3:10].CCN(C(C)C)C(C)C.Cl.[O:21]1[CH:25]=[C:24]([CH2:26][NH2:27])[CH:23]=[N:22]1>ClCCCl.CC(O)=O>[O:21]1[CH:25]=[C:24]([CH2:26][N:27]2[CH2:2][CH:3]([CH2:8][CH2:9][CH3:10])[CH2:4][C:5]2=[O:7])[CH:23]=[N:22]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 222742301-(1,2-Oxazol-4-yl)methanamine--hydrogen chloride (1/1)HCID 23531071357338-44-4

Product 1

HCID 57743052HCID 57743052, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 5-hydroxy-4-propyldihydrofuran-2(3H)-one x252 (0.44 g, 3.0 mmol) in dry DCE (8 ml), DIEA (0.364 g, 2.8 mmol), and several drops AcOH is added to a suspension of 1-isoxazol-4-ylmethanamine hydrochloride x251 (0.46 g, 3.0 mmol) in dry DCE, and NaHB(OAc)3 (0.976 g, 2.3 mmol) is added in 50 min. The reaction mixture is stirred at room temperature for 72 h and washed with 20% K2CO3 (2×25 ml). The aqueous layer is subjected to extraction with dichloromethane (3×30 ml). The combined organic layers are washed with brine (40 ml), dried over Na2SO4, and evaporated. The residue (0.55 g) is purified by chromatography on silicagel (chloroform/ethyl acetate 1/1) to afford 0.202 g of 1-(isoxazol-4-ylmethyl)-4-propylpyrrolidin-2-one 157 (yield 0.202 g, 32%).

Workup

  1. additionis added in 50 min
  2. washwashed with 20% K2CO3 (2×25 ml)
  3. extractionThe aqueous layer is subjected to extraction with dichloromethane (3×30 ml)
  4. washThe combined organic layers are washed with brine (40 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue (0.55 g) is purified by chromatography on silicagel (chloroform/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-caa8627d8f1842a291784dc4c0fa9f02
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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