Sodium borohydride → HCID 58200045, Verbindung

HRID 1907266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907266
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:21])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH:20]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[OH:21])[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH3:9])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 58200034HCID 58200034, Verbindung

Produkt 1

HCID 58200045HCID 58200045, VerbindungAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-tert-butyl 1-(4-bromophenyl)ethyl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (500 mg, 1.11 mmol) in MeOH (20 mL) was added an NaBH4 caplet (1 g, 26 mmol). The mixture was stirred at rt overnight and concentrated under reduced pressure. The residue was partitioned between EtOAc (80 mL) and water (20 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated to leave tert-butyl (S)-1-(4-bromophenyl)ethyl(3-(4-fluorophenyl)-3-hydroxypropyl)carbamate (474 mg, 94%) as an oil. LC-MS (3 min) tR=2.33 min, 454. 452, 380, 378.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc (80 mL) and water (20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d59c18dcd2754bef9c50a6a6f23bdead
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598160B2

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