Triethylamine → (2-(3-(2-Hydroxyethyl)benzyl)-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(5-methylthiophen-2-yl)methanone

HRID 1689274ノート

反応式

HRID 1689274 の反応式
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.Cl.[CH3:13][C:14]1[S:18][C:17]([C:19]([N:21]2[CH2:29][C:25]3([CH2:28][NH:27][CH2:26]3)[O:24][CH2:23][CH2:22]2)=[O:20])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(#N)C>[OH:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:27]1[CH2:26][C:25]2([CH2:29][N:21]([C:19]([C:17]3[S:18][C:14]([CH3:13])=[CH:15][CH:16]=3)=[O:20])[CH2:22][CH2:23][O:24]2)[CH2:28]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67292541(5-Methylthiophen-2-yl)(5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)methanone hydrochloride

生成物 1

HCID 57989289(2-(3-(2-Hydroxyethyl)benzyl)-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(5-methylthiophen-2-yl)methanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-(3-(Bromomethyl)phenyl)ethanol (example 6, step a) (0.281 g) was added to a solution of (5-methylthiophen-2-yl)(5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)methanone hydrochloride (example 33, step h) (0.29 g) and triethylamine (0.42 mL) in acetonitrile (15 mL) at 20° C. and the resultant mixture stirred for 3 hours at 20° C. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 3% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.32 g.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-d78e6cca46654d18b143722f8352e1a0
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

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