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Acetic Acid → 8-[8-(Tert-butyl-dimethyl-silanyloxymethyl)-naphthalen-1-ylmethyl]-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one

HRID 1793581
ノート
印刷プレビュー

反応式

HRID 1793581 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:11](=[O:18])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.[C:19]([SiH2:23][O:24][C:25]([CH3:39])([CH3:38])[C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:35]=1[C:34]([CH:36]=O)=[CH:33][CH:32]=[CH:31]2)([CH3:22])([CH3:21])[CH3:20].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:19]([SiH2:23][O:24][C:25]([CH3:39])([CH3:38])[C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:35]=1[C:34]([CH2:36][N:15]1[CH2:14][CH2:13][C:12]3([N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:9][NH:10][C:11]3=[O:18])[CH2:17][CH2:16]1)=[CH:33][CH:32]=[CH:31]2)([CH3:22])([CH3:21])[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 939151-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 1373285318-(Tert-butyl-dimethyl-silanyloxymethyl)-naphthalene-1-carbaldehyde

生成物 1

HCID 1373285338-[8-(Tert-butyl-dimethyl-silanyloxymethyl)-naphthalen-1-ylmethyl]-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

1-(4-Fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one (0.056 g, 0.22 mmol) and 8-(tert-butyl-dimethyl-silanyloxymethyl)-naphthalene-1-carbaldehyde (0.067 g, 0.22 mmol) were dissolved in dry 1,2-dichloroethane (5 mL). To the reaction mixture was added crashed 4A Molecular Sieve (0.028 g), a catalytic amount of glacial acetic acid. The reaction mixture was stirred at room temperature for 1 hr and it was then added at room temperature sodium triacetoxyborohydride (0.071 g, 0.33 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then partitioned with water and dichloromethane. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via semi-preparative HPLC (aqueous 0.5% TFA/acetonitrile) to yield crude 8-[8-(tert-butyl-dimethyl-silanyloxymethyl)-naphthalen-1-ylmethyl]-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one which was directly used to the next step.

後処理

  1. additionTo the reaction mixture was added
  2. stirringthe reaction mixture was stirred at room temperature for 18 hours
  3. customThe reaction mixture was then partitioned with water and dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto yield a crude oil
  9. customThe crude oil was purified via semi-preparative HPLC (aqueous 0.5% TFA/acetonitrile)

出典と根拠

ORDレコード
ord-4df3871460894af1b8b3d6aebbe29cb1
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07081463B2

反応ノート

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