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

HRID 1892046

반응식

HRID 1892046 반응식
[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

참가 물질

7

반응물 4

HCID 702EthanolHCID 7842Propargyl bromide2회HCID 24758Sodium hydride2회HCID 278563(3-Methyl-1-oxa-4-azaspiro[4.5]decan-3-yl)methanol

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0e5c6747128c4bb480cc197d76148dbe
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507509B2

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