Diboron → N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

HRID 1587945ノート

反応式

HRID 1587945 の反応式
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[C:21](=O)[CH2:20][O:19][CH:18]([C:23]3[N:24]=[C:25]([C:28]([F:31])([F:30])[F:29])[S:26][CH:27]=3)[CH2:17]2)[CH3:15])=[CH:9][CH:8]=1)(OC)=[O:2].B#B>O1CCCC1>[OH:2][CH2:1][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[CH2:21][CH2:20][O:19][CH:18]([C:23]3[N:24]=[C:25]([C:28]([F:29])([F:31])[F:30])[S:26][CH:27]=3)[CH2:17]2)[CH3:15])=[CH:9][CH:8]=1

参加物

4

反応物 2

HCID 6328200DiboronHCID 19974202N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholin-5-one

生成物 1

HCID 19974360N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1 g (0.0022 Mol) of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholin-5-one (diastereomer A) is dissolved in 6 ml of absolute tetrahydrofuran. At room temperature 15 ml (0.015 Mol) of a one molar solution of diborane in tetrahydrofuran is added dropwise within 15-20 minutes. During this the solution heated up to about 35°-40° C. After 30 minutes the mixture is evaporated to dryness and the remaining residue is dissolved in 40 ml of methanol and 2 ml of concentrated hydrochloric acid, and the mixture is left to stand for 30 minutes. While cooling in ice, the mixture is made alkaline with ammonia and is extracted several times by shaking with methylene chloride. The organic phase is dried over sodium sulphate and the base is purified on a silica gel column using toluene/ethyl acetate=7.5:2.5 as eluant.

後処理

  1. temperatureDuring this the solution heated up to about 35°-40° C
  2. customAfter 30 minutes the mixture is evaporated to dryness
  3. dissolutionthe remaining residue is dissolved in 40 ml of methanol
  4. wait2 ml of concentrated hydrochloric acid, and the mixture is left
  5. temperatureWhile cooling in ice
  6. extractionis extracted several times
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. customthe base is purified on a silica gel column

出典と根拠

ORDレコード
ord-faa83ed9604e4371800d86ace70d5351
出典データセット
uspto-grants-1993_06
特許番号
US05219852

反応ノート

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