Iodine → HCID 57950670、化合物

HRID 598864ノート

反応式

HRID 598864 の反応式
Cl.[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:4][C:5](O)=[O:6].[BH4-].[Na+].II>C1COCC1>[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)[CH2:4][CH2:5][OH:6]

参加物

5

反応物 3

HCID 807IodineHCID 2761665(3S)-3-Amino-4-[4-(trifluoromethyl)phenyl]butanoic acid--hydrogen chloride (1/1)HCID 4311764Sodium borohydride

生成物 1

HCID 57950670HCID 57950670、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

(S)-3-Amino-4-(4-(trifluoromethyl)phenyl)butanoic acid hydrochloride (950 mg, 3.84 mmol) and NaBH4 (362 mg, 9.6 mmol) were dissolved in 20 mL THF and cooled to 0° C. A solution of I2 (974 mg, 3.84 mmol) in 5 mL THF was added at 0° C. over a period of 20 minutes. The cooling bath was removed and the reaction was heated at reflux over night. The reaction was cooled to room temperature and carefully hydrolyzed with MeOH until gas evolution ceased. The clear solution was evaporated in vacuo, 20 mL KOH (20%, aqueous) was added, and the reaction was stirred for 3 hours. The reaction was extracted with DCM (3×100 mL), dried over MgSO4 and evaporated. The title compound was obtained as a white solid and used without further purification in the next reaction. LCMS (API-ES) m/z (%): 234.0 (100%, M++H).

後処理

  1. customThe cooling bath was removed
  2. temperaturethe reaction was heated
  3. temperatureat reflux over night
  4. temperatureThe reaction was cooled to room temperature
  5. customThe clear solution was evaporated in vacuo, 20 mL KOH (20%, aqueous)
  6. additionwas added
  7. extractionThe reaction was extracted with DCM (3×100 mL)
  8. dry with materialdried over MgSO4
  9. customevaporated

出典と根拠

ORDレコード
ord-a6d6b1c12688497bbd3b57496d917630
出典データセット
uspto-grants-2011_03
特許番号
US07897619B2

反応ノート

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