Acetone → 117827-79-9

HRID 1381095Notes

Reaction equation

HRID 1381095 reaction equation
C([BH3-])#N.[Na+].[NH2:5][CH:6]1[CH:12]([OH:13])[C:11]2[CH:14]=[CH:15][CH:16]=[C:17]3[NH:18][C:19](=[O:20])[N:9]([C:10]=23)[CH2:8][CH2:7]1.CO.[CH3:23][C:24]([CH3:26])=O>>[CH:24]([NH:5][C@H:6]1[C@H:12]([OH:13])[C:11]2[CH:14]=[CH:15][CH:16]=[C:17]3[NH:18][C:19](=[O:20])[N:9]([C:10]=23)[CH2:8][CH2:7]1)([CH3:26])[CH3:23]

Participants

5

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 13309398HCID 13309398, compound

Product 1

HCID 3086576117827-79-9

Procedure

3 g of sodium cyanoborohydride were added over 15 minutes at 0° to 5° C. to a mixture of 6 g of (6RS, trans) 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,l-j-k][1]-benzazepin-2(1H)-one, 60 ml of methanol and 30 ml of acetone and the mixture was stirred at room temperature for 3 hours and was evaporated to dryness under reduced pressure. The residue was added to 60 ml of water and the mixture was extracted with chloroform. The organic phase was dried and evaporated to dryness to obtain 3.6 g of (6RS,trans) 6-isopropylamino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,l-j-k][1]-benzazepin-2(1H)-one melting at ≃166° C. The latter was dissolved in 60 ml of ethanol and ethyl acetate saturated with hydrogen chloride was added thereto. The mixture was vacuum filtered to obtain 3.7 g of the corresponding hydrochloride melting at ≃270° C. The product was dissolved in hot methanol and ethyl acetate was added to obtain 3.3 g of the said product melting at ≃270° C.

Workup

  1. customwas evaporated to dryness under reduced pressure
  2. additionThe residue was added to 60 ml of water
  3. extractionthe mixture was extracted with chloroform
  4. customThe organic phase was dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8e1155fd407a492e9c647a1ac5860b7a
Source dataset
uspto-grants-1986_04
Patent number
US04585770

Reaction notes

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