Water → HCID 14881409, compound

HRID 1087914Notes

Reaction equation

HRID 1087914 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@H:17]3[N:8]([C:9](=O)[C@@H:10]4[C@H:15]([CH2:16]3)[N:14]([C:21]([NH:23][C@@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])=[O:22])[CH2:13][CH2:12][CH2:11]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@H:17]3[N:8]([CH2:9][C@@H:10]4[C@H:15]([CH2:16]3)[N:14]([C:21]([NH:23][C@@H:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH3:25])=[O:22])[CH2:13][CH2:12][CH2:11]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14543949HCID 14543949, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14881409HCID 14881409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 11.5-g of (8aS,12aS,13aS) 3-methoxy 12-[(R)-(+)-1-phenylethylamino]carbonyl-5,6,8a,9,10,11,12,12a,13,13a decahydroisoquino[2,1-g][1,6]naphthyridin-8-one, in 50 ml of tetrahydrofuran was added slowly to a solution of 2.0-g of lithium aluminum hydride in 75 ml of tetrahydrofuran. The resulting mixture was stirred at reflux for 2 hours, cooled, and treated sequentially with 2.5 ml of water, 2.5 ml of 15% sodium hydroxide, and 7.5 ml of water. The mixture was filtered and the filtrate was evaporated to afford 8.8-g of (8aR,12aS,13aS) 3-methoxy 12-[(R)-(+)-1 phenylethylamino]carbonyl-5,6,8a,9,10,11,12,12a,13,13a decahydro-8H-isoquino[2,1-g][1,6]naphthyridine, a compound of formula (I).

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f07971cacbd542f3848929dd17fc3d2b
Source dataset
uspto-grants-1990_10
Patent number
US04960891

Reaction notes

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