Benzcatechinborane → isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-hydroxy-4-phenylbut-1-en-1-yl]-2-oxo-1,3-oxazinan-3-yl}heptanoate

HRID 1826685Notes

Reaction equation

HRID 1826685 reaction equation
[B]1OC2C(=CC=CC=2)O1.[F:10][C:11]([F:41])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:12](=[O:34])/[CH:13]=[CH:14]/[C@H:15]1[CH2:20][CH2:19][O:18][C:17](=[O:21])[N:16]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29]>C1(C)C=CC=CC=1>[F:41][C:11]([F:10])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH:12]([OH:34])/[CH:13]=[CH:14]/[C@H:15]1[CH2:20][CH2:19][O:18][C:17](=[O:21])[N:16]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29]

Participants

4

Reactant 2

HCID 6327445BenzcatechinboraneHCID 58446090isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-oxo-4-phenylbut-1-en-1-yl]-2-oxo-1,3-oxazinan-3-yl}heptanoate

Product 1

HCID 11213173isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-hydroxy-4-phenylbut-1-en-1-yl]-2-oxo-1,3-oxazinan-3-yl}heptanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of catecholborane (107 mg) in toluene (1 mL) was added (S)-2-methyl-CBS-oxaborolidine (1M in toluene, 0.89 mL) under N2 at −78° C. and the mixture was stirred at the temperature for 1 h. Isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-oxo-4-phenylbut-1-en-1-yl]-2-oxo-1,3-oxazinan-3-yl}heptanoate (200 mg) in toluene (2 mL) was added via a cannula slowly and the mixture was stirred for an additional hour and quenched with 1N HCl. The mixture was allowed to warm to room temperature and extracted with DCM (2×). The organic layers were dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue purified by column chromatography (80–100% ethyl acetate/hexanes) to give the title compound. MS (+ESI): m/z 454 (M+1)+.

Workup

  1. stirringthe mixture was stirred for an additional hour
  2. customquenched with 1N HCl
  3. extractionextracted with DCM (2×)
  4. dry with materialThe organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue purified by column chromatography (80–100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-18806b4e5ed34bb8bf5cc255f027711c
Source dataset
uspto-grants-2006_05
Patent number
US07053085B2

Reaction notes

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