(7S)-3-((S)-1-(4-bromophenyl)ethyl)-7-((2-methyloxiran-2-yl)methyl)-7-phenyl-1,3-oxazepan-2-one → (S)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-hydroxy-2-methylpropyl)-7-phenyl-1,3-oxazepan-2-one

HRID 219629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219629
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:16][CH2:15][CH2:14][C@:13]([CH2:23][C:24]3([CH3:27])[CH2:26][O:25]3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:12][C:11]2=[O:28])[CH3:9])=[CH:4][CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:16][CH2:15][CH2:14][C@:13]([CH2:23][C:24]([OH:25])([CH3:26])[CH3:27])([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:12][C:11]2=[O:28])[CH3:9])=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 59190382(7S)-3-((S)-1-(4-bromophenyl)ethyl)-7-((2-methyloxiran-2-yl)methyl)-7-phenyl-1,3-oxazepan-2-one

Produkt 1

HCID 59190379(S)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-hydroxy-2-methylpropyl)-7-phenyl-1,3-oxazepan-2-oneAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (7S)-3-((S)-1-(4-bromophenyl)ethyl)-7-((2-methyloxiran-2-yl)methyl)-7-phenyl-1,3-oxazepan-2-one (280 mg, 0.63 mmol) in THF (10 mL) was added dropwise 1 M LiEt3BH in THF (Super-hydride, 6.3 mL, 6.3 mmol) at 0° C. under N2 for 30 min. The resulting solution was stirred at room temperature for 1 h, quenched with H2O2 (7 mL), diluted with (CH3)3COCH3 (30 mL), washed with water, 30% aq Na2S2O3 and brine. The organic phase was dried over Na2SO4, and concentrated to give the crude product, which was purified by prep TLC afford (S)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-hydroxy-2-methylpropyl)-7-phenyl-1,3-oxazepan-2-one (150 mg, 53%). (S)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-hydroxy-2-methylpropyl)-7-phenyl-1,3-oxazepan-2-one. LC-MS Method 30-90 tR=1.199 min, m/z=470; 1H NMR (CDCl3) d 0.83 (s, 3H), 1.05 (m, 1H), 1.13 (s, 3H), 1.42 (m, 1H), 1.48 (d, 3H), 2.1-2.35 (m, 4H), 2.72 (m, 1H), 3.13 (m, 1H), 3.95 (s, 1H), 5.50 (m, 1H), 7.02 (d, 2H), 7.22 (m, 1H), 7.30 (m, 2H), 7.32-7.48 (m, 4H).

Aufarbeitung

  1. customquenched with H2O2 (7 mL)
  2. additiondiluted with (CH3)3COCH3 (30 mL)
  3. washwashed with water, 30% aq Na2S2O3 and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by prep TLC

Quellen und Nachweise

ORD-Eintrag
ord-855a204f6e7341ce9850c179b3ea97ec
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202857B2

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