Carbon Tetrachloride → HCID 57779814、化合物

HRID 552906ノート

反応式

HRID 552906 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH:13](O)[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:40]>C(#N)C.ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH:13]([Cl:40])[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57779818HCID 57779818、化合物

生成物 1

HCID 57779814HCID 57779814、化合物

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

At 70° C., 146.0 mg (0.52 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-6-hydroxy-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one (cf. I-16) and 274.2 mg (1.05 mmol) of triphenylphosphine are stirred in a mixture of 2.5 ml of acetonitrile and 2.5 ml of carbon tetrachloride. After cooling to room temperature, the mixture is diluted with dichloromethane and washed successively with dilute aqueous ammonium hydroxide solution and saturated sodium chloride solution: the organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 063 m) using the mobile phase ethyl acetate and subsequent preparative HPLC gives both possible diastereomers of 4-[(6-chloropyridin-3-yl)methyl]-6-chloro-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one: (a) 4 mg of diastereomer A (3% of theory) and (b) 15 mg of diastereomer B (9% of theory). In addition, (c) 10 mg (7% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-7,7a-dihydrofuro[3,2-b]pyridin-2(4H)-one are obtained.

後処理

  1. washwashed successively with dilute aqueous ammonium hydroxide solution and saturated sodium chloride solution
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 063 m)

出典と根拠

ORDレコード
ord-b1c7f56436544b62ba3485e7073e3bba
出典データセット
uspto-grants-2011_05
特許番号
US07951951B2

反応ノート

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