Iodine → HCID 57950670, compound

HRID 598864Notes

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

(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).

Workup

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

Sources & evidence

ORD record: ord-a6d6b1c12688497bbd3b57496d917630
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897619B2

Reaction notes

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