Water → HCID 58109499, compound

HRID 2037591Notes

Reaction equation

HRID 2037591 reaction equation
S(C)C.CC(CC)=C.[CH2:9]([C:12]1([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])[CH2:14][CH2:13]1)[CH:10]=[CH2:11].[OH2:35]>C1COCC1>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[CH2:19][N:15]1[CH2:14][CH2:13][C:12]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)([CH2:9][CH2:10][CH2:11][OH:35])[O:17][C:16]1=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 112402-Methyl-1-buteneHCID 58109404HCID 58109404, compound

Product 1

HCID 58109499HCID 58109499, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirred solution of BH3.Me2S (0.7 mL, 7.0 mmol) in dry THF (7 mL) was cooled in an ice bath and 2 M 2-methylbutene in THF (7 mL, 14 mmol) was added dropwise over 3 min. The mixture was stirred in the ice bath for 1.5 h. An aliquot of this solution (0.25 mL, 0.12 mmol) was added to an ice-cold solution of 6-allyl-3-(2,4-dichlorobenzyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (3.2 mg, 8.0 μmol) in dry THF (0.5 mL). The mixture was stirred overnight at rt. Water (2 mL) was added and the mixture was stirred for 3 h. Solid NaBO3.H2O (10 mg) was added. The mixture was stirred overnight, applied to a 10-mL ChemElut cartridge and eluted with CH2Cl2 (20 mL). The eluate was concentrated and the residue was purified by prep HPLC to afford 3-(2,4-dichlorobenzyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (1.3 mg, 39%). LC-MS Method 1 tR=1.78 min, m/z=368; 1H NMR (CDCl3) 1.37 (m, 1H), 1.66 (m, 1H), 1.99 (m, 2H), 2.30 (m, 2H), 2.92 (m, 1H), 3.10 (m, 1H), 3.58 (t, 2H), 4.50 (d, 1H), 4.63 (d, 1H), 6.90-7.35 (7H).

Workup

  1. stirringthe mixture was stirred for 3 h
  2. stirringThe mixture was stirred overnight
  3. washeluted with CH2Cl2 (20 mL)
  4. concentrationThe eluate was concentrated
  5. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-99aba037be3a43f59aebc91b9f25bfd0
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…