Methanol → HCID 22182534, compound

HRID 585048Notes

Reaction equation

HRID 585048 reaction equation
C([O:3][C:4]([CH:6]1[CH2:19][CH2:18][C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH2:12][CH2:11][CH2:10]3)[O:7]1)=O)C.[BH4-].[Li+].CO>O1CCCC1.C(OCC)(=O)C>[NH:13]1[C:14]2[C:9](=[C:8]3[C:17](=[CH:16][CH:15]=2)[CH2:18][CH2:19][CH:6]([CH2:4][OH:3])[O:7]3)[CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 69658039HCID 69658039, compound

Product 1

HCID 22182534HCID 22182534, compoundYield 122.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1,3,4,6,7,8-hexahydro-2H-5-oxa-1-aza-phenanthrene-6-carboxylic acid ethyl ester (0.80 g, 3.1 mmole) in 25 mL of tetrahydrofuran was added 0.22 g (10 mmole) of lithium borohydride. The mixture was stirred for 48 hours at room temperature. Methanol (5 mL) was added and stirring at room temperature continued for an additional hour. The mixture was then diluted to 300 mL with ethyl acetate and washed with 100 mL portions of water and saturated brine and dried over sodium sulfate. Filtration and concentration in vacuum gave 0.83 g of the title compound as a white solid. 1H-NMR (CDCl3): doublet 6.65 δ (1H); doublet 6.1 δ (1H); multiplet 4.1 δ (1H); multiplet 3.8 δ (2H); multiplet 3.2 δ (2H); broad singlet 2.8 δ (1H); multiplet 2.55 δ (4H); multiplet 1.9 δ (2H); multiplet 1.2 δ (2H).

Workup

  1. stirringstirring at room temperature
  2. waitcontinued for an additional hour
  3. washwashed with 100 mL portions of water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration in vacuum

Sources & evidence

ORD record
ord-a8e4c69e80f2419fb5dd0d4c27054980
Source dataset
uspto-grants-2005_08
Patent number
US06930109B2

Reaction notes

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