Tetrahydrofuran → HCID 58256490, compound

HRID 2045832Notes

Reaction equation

HRID 2045832 reaction equation
C(BC(C(C)C)C)(C(C)C)C.[CH2:12]([C:15]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[O:20][C:19](=[O:21])[N:18]([N:22]([CH3:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH2:16]1)[CH:13]=[CH2:14].C1C[O:40]CC1>>[F:36][C:33]1[CH:32]=[CH:31][C:30]([C:15]2([CH2:12][CH2:13][CH2:14][OH:40])[O:20][C:19](=[O:21])[N:18]([N:22]([CH3:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:16]2)=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 192733Bis(1,2-dimethylpropyl)boraneHCID 44137272HCID 44137272, compound

Product 1

HCID 58256490HCID 58256490, compound

Procedure

At 0° C., 2M 2-methyl-2-butene in THF (15 mL, 30 mmol) was added to BH3.DMS (1.5 mL, 15 mmol, 10M) in THF (3 mL) and stirred for 1 h to afford a 0.83 M THF solution of disiamylborane. In a separate flask, disiamylborane (0.1 mL, 0.08 mmol) was added to 6-allyl-6-(4-fluorophenyl)-3-(methyl(phenyl)amino)-1,3-oxazinan-2-one (6 mg, 0.018 mmol) in THF (1 mL) at 0° C. The reaction was warmed to rt overnight. The reaction was cooled to 0° C. and quenched with H2O (1 mL) and stirred for 15 min at rt. NaBO3 (22 mg, 0.22 mmol) was added and the reaction was stirred for 2 h. The solvent was evaporated and the crude material purified by prep HPLC to afford 6-(4-fluorophenyl)-6-(3-hydroxypropyl)-3-(methyl(phenyl)amino)-1,3-oxazinan-2-one (1.16 mg). LC/MS Method 1 tR=1.51 min m/z=359 (M+1).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with H2O (1 mL)
  3. stirringthe reaction was stirred for 2 h
  4. customThe solvent was evaporated
  5. customthe crude material purified by prep HPLC

Sources & evidence

ORD record
ord-9505697c855b4a87846be91fbdadd3f7
Source dataset
uspto-grants-2013_11
Patent number
US08592409B2

Reaction notes

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