Tetrahydrofuran → HCID 59532390, compound

HRID 2193447Notes

Reaction equation

HRID 2193447 reaction equation
[CH2:1]([C@@:4]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:12][CH3:13])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[O:27]1CCCC1>>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:1][CH2:2][CH2:3][OH:27])([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:9][C:8]2=[O:10])[CH2:12][CH3:13])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 59532387HCID 59532387, compound

Product 1

HCID 59532390HCID 59532390, compoundYield 15%

Procedure

To a solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)propyl)-6-phenyl-1,3-oxazinan-2-one (100 mg, 0.242 mmol) in tetrahydrofuran (10 mL) was added BH3 THF (3 mL, 1 mol/L) at 0° C. under nitrogen. The formed mixture was stirred for 2 h. Then the reaction was quenched by water, followed by 3 mol/L NaOH and H2O2 (3 mL). The PH of the mixture was adjusted to <7 with 5% HCl. The organic phase was separated, extracted by EtOAc, and concentrated to give the crude product, which was purified by preparative HPLC to give (R)-3-((S)-1-(4-bromophenyl)propyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (15 mg, 15%). LC-MS Method 3 tR=1.36, min, m/z=432, 434; 1H NMR (CDCl3): δ=0.99 (t, 3H), 1.29 (m, 1H), 1.63 (m, 1H), 1.98 (m, 4H), 2.20-2.42 (m, 2H), 2.48 (m, 1H), 3.08 (m, 1H), 3.49 (m, 1H), 5.30 (m, 1H), 6.92 (m, 2H), 7.26 (m, 4H), 7.35 (m, 2H).

Workup

  1. customThen the reaction was quenched by water
  2. customThe organic phase was separated
  3. extractionextracted by EtOAc
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-b2a9caab0c8a41d5b0a3cdd99669cf7f
Source dataset
uspto-grants-2012_12
Patent number
US08329897B2

Reaction notes

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