Potassium Carbonate → (3S,4R)-3-Hydroxy-4-(2H-imidazol-2-ylsulfanyl)-2,2-dimethyl-chroman-6-carbonitrile

HRID 1159595ノート

反応式

HRID 1159595 の反応式
[CH3:1][C:2]1([CH3:15])[O:11][C:10]2[C:5](=[CH:6][C:7]([C:12]#[N:13])=[CH:8][CH:9]=2)[C@@H:4]2[O:14][C@H:3]12.[NH:16]1[CH:20]=[CH:19][NH:18][C:17]1=[S:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:14][C@@H:3]1[C@H:4]([S:21][CH:17]2[N:18]=[CH:19][CH:20]=[N:16]2)[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:12]#[N:13])[CH:6]=2)[O:11][C:2]1([CH3:15])[CH3:1]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 12013862-MercaptoimidazoleHCID 9837089(1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

生成物 1

HCID 68644174(3S,4R)-3-Hydroxy-4-(2H-imidazol-2-ylsulfanyl)-2,2-dimethyl-chroman-6-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(S,S)-2,2-Dimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene-6-carbonitrile (1 mmoL), 1,3-dihydro-imidazole-2-thione (1 mmoL) and anhydrous K2CO3 (1.5 mmoL) in DMF (5 mL) were heated at 100° C. for 4˜6 hrs. The solid was filtered off and the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated NH4Cl, brine, then dried over anhydrous Na2SO4, filtered and concentrated to yield a yellow oil. Silica gel chromatography separation yielded the title compound as a white solid.

後処理

  1. filtrationThe solid was filtered off
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated NH4Cl, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow oil
  8. customSilica gel chromatography separation

出典と根拠

ORDレコード
ord-9305f411534b41ee978505cf1fe25b0b
出典データセット
uspto-grants-2010_10
特許番号
US07812183B2

反応ノート

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