Methanol → 3-Ethyl-1-(2-hydroxy-ethyl)-3-(3-benzyloxyphenyl)-azepan-2-one

HRID 1594914Notes

Reaction equation

HRID 1594914 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]([CH2:25][CH3:26])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)[C:5]1=[O:27])[CH:2]=C.[BH4-].[Na+].C[OH:31]>>[CH2:25]([C:6]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)[CH2:7][CH2:8][CH2:9][CH2:10][N:4]([CH2:1][CH2:2][OH:31])[C:5]1=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 217063061-Allyl-3-ethyl-3-(3-benzyloxy-phenyl)-azepan-2-one

Product 1

HCID 217062773-Ethyl-1-(2-hydroxy-ethyl)-3-(3-benzyloxyphenyl)-azepan-2-one

Conditions

Temperature
-40 °C

Procedure

A solution of 1-allyl-3-ethyl-3-(3-benzyloxy-phenyl)-azepan-2-one, as described in Step B above, (0.87 g, 2.4 mmol) in MeOH (20 mL) at −78° C. was saturated with 03 for 25 min. The solution was warmed to −40° C. for 10 min then NaBH4 (0.363 g, 9.6 mmol) was added and the reaction mixture was stirred at 25° C. for 1 hr. The MeOH was removed in vacuo , and the residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound after chromatography on silica gel eluting with hexane/EtOAc, 1/1.

Workup

  1. customat −78° C.
  2. customThe MeOH was removed in vacuo
  3. customthe residue was partitioned between EtOAc and saturated NaHCO3 solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-6bca3a3830cd40f6a92b14d9413bd5df
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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