Hydrochloric Acid → HCID 20464739, compound

HRID 325434Notes

Reaction equation

HRID 325434 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]([C:10](C(OC)C2N(C)C3C(=O)C4C=CC(C)=CC=4OCC=3C=2)=[O:11])OC)=[CH:5][C:4]2[CH2:32][O:33][C:34]3[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:35]=3[C:36](=[O:37])[C:3]1=2.[BH4-].[Na+].Cl.Cl(O)(=O)(=O)=O>CCOCC.C(Cl)Cl.CO>[CH3:1][N:2]1[C:6]([CH2:7][CH:10]=[O:11])=[CH:5][C:4]2[CH2:32][O:33][C:34]3[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:35]=3[C:36](=[O:37])[C:3]1=2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24247Perchloric AcidHCID 4311764Sodium borohydrideHCID 131713481HCID 131713481, compound

Product 1

HCID 20464739HCID 20464739, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred, cold mixture of [1,7-dimethyl]-4,10-dihydro-10-oxo-1H[1]benzoxepino[4,3-b]pyrrole-2-yl-methoxymethyl ketone (3.0 g, 0.01 m) and methanol is added sodium borohydride (0.114 g, 0.003 m) over ca. 15 minutes. The reaction mixture is allowed to warm slowly to room temperature over several hours. Excess dilute hydrochloric acid and methylene chloride are added, the layers separated, and the methylene chloride layer concentrated in vacuo to the corresponding crude alcohol which is dehydrated with pyridine-phosphorus oxychloride to yield the intermediate, an enol-ether. This is taken up in ether and treated with perchloric acid (Ber. 95 (1962) 2514) to yield 1,7-dimethyl-4,10-dihydro-10-oxo-1H[1]benzoxepino[4,3-b]pyrrole-2-acetaldehyde, which is oxidized according to Example 24 to give I.

Workup

  1. customthe layers separated
  2. concentrationthe methylene chloride layer concentrated in vacuo to the corresponding crude alcohol which
  3. customto yield the intermediate

Sources & evidence

ORD record
ord-b4f90dc620274675814f4478f96f31b0
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

Loading…