Benzyl acetone → HCID 13067575, compound

HRID 638005Notes

Reaction equation

HRID 638005 reaction equation
[ClH:1].[NH2:2][C@@H:3]1[CH2:12][CH2:11][C:10]2[C:9]([C:13]([NH2:15])=[O:14])=[C:8]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:7]=[CH:6][C:5]=2[C@H:4]1[OH:24].[CH2:25]([CH2:32][C:33](=O)[CH3:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([BH3-])#N.[Na+]>CO.O>[ClH:1].[CH2:17]([O:16][C:8]1[CH:7]=[CH:6][C:5]2[C@@H:4]([OH:24])[C@H:3]([NH:2][CH:33]([CH3:34])[CH2:32][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:12][CH2:11][C:10]=2[C:9]=1[C:13]([NH2:15])=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 17355Benzyl acetoneHCID 5003444Sodium cyanoborohydrideHCID 13067471HCID 13067471, compound

Product 1

HCID 13067575HCID 13067575, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 30 ml of methanol was dissolved 1 g of trans-6-amino-2-benzyloxy-5-hydroxy-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride, followed by addition of 5 g of benzylacetone. Then, under ice-cooling, 1 g of sodium cyanoborohydride was added and the mixture was allowed to stand at room temperature overnight. The reaction mixture was diluted with 300 ml of water and extracted 3 times with 30 ml of CHCl3. The CHCl3 layers were combined, washed with water, dried and concentrated under reduced pressure. The residue was dissolved in 50 ml of ethyl ether, followed by addition of 5 ml of 20% ethanolic hydrochloric acid, whereby 0.84 g of trans-2-benzyloxy-5-hydroxy-6-(1-methyl-3-phenylpropylamino)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride was obtained as colorless crystals, m.p. 215°-218° C.

Workup

  1. temperatureThen, under ice-cooling
  2. extractionextracted 3 times with 30 ml of CHCl3
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 50 ml of ethyl ether
  7. additionfollowed by addition of 5 ml of 20% ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-7f568bcc25ad4f91b5ad0ca879135102
Source dataset
uspto-grants-1985_12
Patent number
US04559361

Reaction notes

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