(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 219629Notes

Reaction equation

HRID 219629 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

HCID 59190379(S)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-hydroxy-2-methylpropyl)-7-phenyl-1,3-oxazepan-2-oneYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-855a204f6e7341ce9850c179b3ea97ec
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

Loading…