Tetrahydrofuran → (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1046074Notes

Reaction equation

HRID 1046074 reaction equation
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[O:26]1CCCC1>>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:1][CH2:2][CH2:3][OH:26])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 59532360(R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 59532368(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-oneYield 36.4%

Procedure

To a solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (11.37 g, 28.5 mmol) in tetrahydrofuran (250 mL) was added BH3 THF (80 mL, 1 mol/L, 4 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred for 2 h, quenched by addition of water. NaOH solution (3 mol/L, 16 mL) and H2O2 (45 mL) were added to the above mixture. When reaction was over, the mixture was extracted with EtOAc. The combined organic layer was concentrated to give the crude product, which was purified by column chromatography to give (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (4.32 g, 36.4%). 1H NMR: (400 MHz, CDCl3): δ1.48 (t, 3H), 1.53 (m, 1H), 1.73 (m, 1H), 1.93-1.98 (m, 2H), 2.17-2.28 (m, 3H), 3.57 (t, 2H), 5.59 (m, 1H), 6.72 (m, 2H), 7.20 (m, 2H), 7.25-7.37 (m, 5H).

Workup

  1. customquenched by addition of water
  2. additionNaOH solution (3 mol/L, 16 mL) and H2O2 (45 mL) were added to the above mixture
  3. customWhen reaction
  4. extractionwas extracted with EtOAc
  5. concentrationThe combined organic layer was concentrated
  6. customto give the crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1190aca1d78948539d14922e59540a5c
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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