Hydrogen Peroxide → HCID 21706229, compound

HRID 1594903Notes

Reaction equation

[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]([CH2:19][CH3:20])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:5]1=[O:21])[CH:2]=[CH2:3].B.C1C[O:26]CC1.[OH-].[Na+].OO>C1COCC1.CCO>[CH2:19]([C:6]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:7][CH2:8][CH2:9][CH2:10][N:4]([CH2:1][CH2:2][CH2:3][OH:26])[C:5]1=[O:21])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-allyl-3-ethyl-3-(3-methoxy-phenyl)-azepan-2-one (as described above in Step A) (0.83 g, 2.89 mmol) in THF (20 mL) at 0° C. was added BH3.THF (1M, 2.85 mL, 2.89 mmol) with stirring. After 1 hr at 25° C. the reaction mixture was cooled to 0° C. and EtOH (5 mL), 1M NaOH (5 mL), and 30% H2O2 (10 mL) were added. The reaction mixture was stirred for 1 hr at 25° C. The solvents were removed in vacuo and the residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine and dried (MgSO4), the solvents removed in vacuo and the crude product chromatographed on silica gel with hexane and ethyl acetate 1:1 to obtain the title compound.

Workup

stirringThe reaction mixture was stirred for 1 hr at 25° C
customThe solvents were removed in vacuo
customthe residue was partitioned between EtOAc and saturated NaHCO3 solution
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
customthe solvents removed in vacuo
customthe crude product chromatographed on silica gel with hexane and ethyl acetate 1:1

Sources & evidence

ORD record: ord-58f4f11794e34ab1ae8e743f67722f47
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284755B1

Reaction notes

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