Borane;tetrahydrofuran → 3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-isopropyl-1,3-oxazinan-2-one

HRID 1187933Notes

Reaction equation

HRID 1187933 reaction equation
[CH2:1]([C:4]1([CH:20]([CH3:22])[CH3:21])[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].B.C1C[O:27]CC1>C1COCC1>[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:27])([CH:20]([CH3:22])[CH3:21])[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 596357496-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-1,3-oxazinan-2-one

Product 1

HCID 596357063-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-isopropyl-1,3-oxazinan-2-oneYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-1,3-oxazinan-2-one (480 mg, 1.315 mmol) in THF (5 mL) was added BH3.THF (5.3 mL, 5.3 mmol) at 0° C. under N2. The reaction mixture was stirred for 2 h, and quenched with water, 3 M aq NaOH (1 mL), and H2O2 (5 mL). The resulting mixture was stirred for 2 h, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by prep TLC to give 3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-isopropyl-1,3-oxazinan-2-one. (110 mg, 22% yield). 1H NMR (CDCl3): δ0.88 (m, 6H), 1.45 (m, 3H), 1.60 (m, 4H), 1.71 (m, 1H), 1.82 (m, 1H), 1.99 (m, 1H), 2.63 (m, 1H), 3.03 (m, 1H), 3.59 (m, 2H), 5.68 (m, 1H), 7.13 (d, 2H), 7.40 (d, 2H),

Workup

  1. customquenched with water, 3 M aq NaOH (1 mL), and H2O2 (5 mL)
  2. stirringThe resulting mixture was stirred for 2 h
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude product, which
  9. customwas purified by prep TLC

Sources & evidence

ORD record
ord-7c6bc9b8e4e3437c8490ac0dbc61a3e8
Source dataset
uspto-grants-2014_03
Patent number
US08673899B2

Reaction notes

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