Hydrochloric Acid → 3-Hydroxymethyl-3,4-dihydro-2H-naphtho[1,8-cd]azepin-1-one

HRID 660582Notes

Reaction equation

HRID 660582 reaction equation
C[O:2][C:3]([CH:5]1[C:14]2[CH2:15][N:16]=[CH:17][CH:18]=[C:12]3[C:13]=2[C:8](=[CH:9][CH:10]=[CH:11]3)[C:7](=[O:19])[CH2:6]1)=O.[Li+].[BH4-].C(OCC)(=O)C.Cl>CO>[OH:2][CH2:3][CH:5]1[C:14]2[CH2:15][N:16]=[CH:17][CH:18]=[C:12]3[C:13]=2[C:8](=[CH:9][CH:10]=[CH:11]3)[C:7](=[O:19])[CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 866325801-Oxo-1,2,3,4-tetrahydronaphtho[1,8-cd]azepine-3-carboxylic Acid Methyl Ester

Product 1

HCID 866325813-Hydroxymethyl-3,4-dihydro-2H-naphtho[1,8-cd]azepin-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-oxo-1,2,3,4-tetrahydronaphtho[1,8-cd]azepine-3-carboxylic acid methyl ester (70 mg, 0.28 mmol) in MeOH (5 mL) is added LiBH4 (18.3 mg, 0.83 mmol) and the mixture is stirred at RT for 1 h. Ethyl acetate is added followed by ice and 1N HCl. The mixture is washed with brine then water and the organic phase is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by preparative HPLC to give the title compound.

Workup

  1. washThe mixture is washed with brine
  2. dry with materialwater and the organic phase is dried over magnesium sulfate
  3. customThe solvent is removed under reduced pressure
  4. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-f7bbfb9b39b6448cb239f004c59f58a8
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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