Tetrahydrofuran → HCID 58109684, compound

HRID 2037562Notes

Reaction equation

HRID 2037562 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][O:8][CH2:9][CH2:10][CH2:11][C@@:12]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]3[CH:26]=[CH:25][C:24]([CH:27]=[CH2:28])=[CH:23][CH:22]=3)[CH3:20])[CH2:14][CH2:13]2)=[CH:5][CH:4]=1.C1C[O:40]CC1>>[OH:40][CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([C@@H:19]([N:15]2[CH2:14][CH2:13][C@:12]([CH2:11][CH2:10][CH2:9][O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:36][CH:35]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:17][C:16]2=[O:18])[CH3:20])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 58109533HCID 58109533, compound

Product 1

HCID 58109684HCID 58109684, compoundYield 96%

Procedure

To a solution of (R)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (260 mg, 0.536 mmol) in THF (3 mL) was added BH3 THF (1.6 mL, 1 mol/L) at 0° C. under nitrogen atmosphere. The formed mixture was stirred for 2 h. The reaction was quenched with water. Then aqueous NaOH solution (1 mol/L, 2 mL) and H2O2 (1 mL) were added to the above mixture. The resulting mixture was stirred for 1.5 h. The mixture was extracted with EtOAc and the combined organic phase was concentrated to give crude (R)-3-((S)-1-(4-(2-hydroxyethyl)phenyl)ethyl)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-1,3-oxazinan-2-one (260 mg, 96%), which was used for the next step without purification. 1H NMR (CDCl3): δ=1.32 (m, 2H), 1.41 (d, 3H), 1.89 (m, 2H), 2.12 (m, 1H), 2.22 (m, 2H), 2.68 (m, 1H), 2.81 (m, 1H), 3.27 (m, 2H), 3.72 (s, 3H), 4.26 (s, 2H), 5.53 (q, 1H), 6.71-6.88 (m, 5H), 7.13 (m, 2H), 7.26 (m, 4H).

Workup

  1. customThe reaction was quenched with water
  2. additionThen aqueous NaOH solution (1 mol/L, 2 mL) and H2O2 (1 mL) were added to the above mixture
  3. stirringThe resulting mixture was stirred for 1.5 h
  4. extractionThe mixture was extracted with EtOAc
  5. concentrationthe combined organic phase was concentrated

Sources & evidence

ORD record
ord-295ad5505a4347db933f17f4c7a70f4a
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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