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

HRID 1594905Notes

Reaction equation

HRID 1594905 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]=C.[BH4-].[Na+].C[OH:25]>>[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][OH:25])[C:5]1=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 217062791-Allyl-3-ethyl-3-(3-methoxy-phenyl)-azepan-2-one

Product 1

HCID 217061943-Ethyl-1-(2-hydroxy-ethyl)-3-(3-methoxy-phenyl)-azepan-2-one

Conditions

Temperature
-40 °C

Procedure

A solution of 1-allyl-3-ethyl-3-(3-methoxy-phenyl)-azepan-2-one (as described in Example 49, Step A) (0.9 g, 3.1 mmol) in MeOH (20 mL) at −78° C. was saturated with 03 for 20 min. The solution was warmed to −40° C. for 10 min then NaBH4 (0.36 g, 9.4 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.

Workup

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

Sources & evidence

ORD record
ord-fc2ae5dff3ee462cb5a3f79f2212e3b7
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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