Ethanol → 3-Methyl-3-prop-2-ynyloxymethyl-1-oxa-4-aza-spiro[4.5]decane

HRID 1892046ノート

反応式

HRID 1892046 の反応式
[H-].[Na+].[CH3:3][C:4]1([CH2:14][OH:15])[NH:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6][CH2:5]1.[CH2:16](Br)[C:17]#[CH:18].C(O)C>C1COCC1.C(OCC)C>[CH3:3][C:4]1([CH2:14][O:15][CH2:18][C:17]#[CH:16])[NH:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6][CH2:5]1

参加物

7

反応物 4

HCID 702EthanolHCID 7842Propargyl bromide2 回HCID 24758Sodium hydride2 回HCID 278563(3-Methyl-1-oxa-4-azaspiro[4.5]decan-3-yl)methanol

生成物 1

HCID 595654083-Methyl-3-prop-2-ynyloxymethyl-1-oxa-4-aza-spiro[4.5]decane

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (55% in dispersion in oil) (0.636 g) was added portion wise to a solution of (3-methyl-1-oxa-4-aza-spiro[4.5]dec-3-yl)-methanol (2.0 g) in dry THF (30 ml) at 0° C. The reaction mixture was stirred at R.T. for 50′. Propargyl bromide (0.972 ml) was added dropwise at 0° C. and the resulting mixture was stirred at R.T. for 2 h 30. Additional sodium hydride (55% in dispersion in oil) (0.047 g) and propargyl bromide (0.081 ml) were added at 0° C. followed by the heating of the reaction mixture at 40-45° C. for 1 hr allowed to reach reaction completion. The reaction mixture was treated with abs. Ethanol (4 ml) and diluted with diethyl ether. The resulting insoluble residue was filtered off and the filtrate was concentrated in vacuo to give 2.89 g of crude residue which was purified by column chromatography (hexane/ethyl acetate 1:1) to yield 2.33 g of 3-Methyl-3prop-2-ynyloxymethyl-1-oxa-4-aza-spiro[4.5]decane as an orange liquid.

後処理

  1. stirringthe resulting mixture was stirred at R.T. for 2 h 30
  2. temperatureheating of the reaction mixture at 40-45° C. for 1 hr
  3. customreaction completion
  4. additionThe reaction mixture was treated with abs
  5. filtrationThe resulting insoluble residue was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customto give 2.89 g of crude residue which
  8. customwas purified by column chromatography (hexane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-0e5c6747128c4bb480cc197d76148dbe
出典データセット
uspto-grants-2013_08
特許番号
US08507509B2

反応ノート

読み込み中…