4-Benzyloxy-1-{2-oxo-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one → 4-Benzyloxy-1-{2-hydroxy-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one

HRID 564168Notes

Reaction equation

HRID 564168 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16](=[O:34])[C:17]2[CH:33]=[CH:32][C:20]3[CH2:21][CH2:22][N:23]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:24][CH2:25][C:19]=3[CH:18]=2)[C:11](=[O:35])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[BH4-]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH:16]([OH:34])[C:17]2[CH:33]=[CH:32][C:20]3[CH2:21][CH2:22][N:23]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:24][CH2:25][C:19]=3[CH:18]=2)[C:11](=[O:35])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 580428744-Benzyloxy-1-{2-oxo-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-oneHCID 131720715CID 131720715

Product 1

HCID 580427894-Benzyloxy-1-{2-hydroxy-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.20 g (2.48 mmol) 4-benzyloxy-1-{2-oxo-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one (example 22.1) in 10 mL MeOH is added 94 mg (2.48 mmol) sodium-borohydride and the mixture is stirred 2 h at RT. The solvent is evaporated, the residue is taken up in EtOAc and water. The layers are separated, the organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via chromatography (silica gel; EE/MeOH 8:2).

Workup

  1. customThe solvent is evaporated
  2. customThe layers are separated
  3. dry with materialthe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe residue is purified via chromatography (silica gel; EE/MeOH 8:2)

Sources & evidence

ORD record
ord-c3a98f83268b4f32b9d5f498cca645bd
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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