Sodium borohydride → HCID 86744451, compound

HRID 1111549Notes

Reaction equation

HRID 1111549 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([C:15]3[CH:24]=[CH:23][C:22]4[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=4[CH:16]=3)=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:29]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:42]([C:44]3[CH:53]=[CH:52][C:51]4[C:50]([CH3:55])([CH3:54])[CH2:49][CH2:48][C:47]([CH3:57])([CH3:56])[C:46]=4[CH:45]=3)=[O:43])[CH:38]=2)[C:33]=1[CH2:58][CH3:59])(=[O:31])=[O:30])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]([C:15]3[CH:24]=[CH:23][C:22]4[C:21]([CH3:25])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:27])([CH3:28])[C:17]=4[CH:16]=3)[OH:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:29]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([CH:42]([OH:43])[C:44]3[CH:53]=[CH:52][C:51]4[C:50]([CH3:55])([CH3:54])[CH2:49][CH2:48][C:47]([CH3:57])([CH3:56])[C:46]=4[CH:45]=3)[CH:38]=2)[C:33]=1[CH2:58][CH3:59])(=[O:31])=[O:30])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86744452HCID 86744452, compound

Product 1

HCID 86744451HCID 86744451, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 200 mg of ethyl 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) carbonyl]-2-naphthylsulfone, obtained in accordance with Example XIV, in 30 cm3 of methanol cooled to 0° C., there are added 100 mg of sodium borohydride. The reaction mixture is maintained under stirring for 30 minutes, then it is returned to ambient temperature. After verification by thin layer chromatography of the disappearance of the starting carbonyl product, the alcohol is evaporated under reduced pressure and the residue is taken up in 100 cm3 of water and acidified with a solution of 1N HCl. The resulting precipitate is filtered and dried under a vacuum.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customis returned to ambient temperature
  3. customAfter verification by thin layer chromatography of the disappearance of the starting carbonyl product, the alcohol is evaporated under reduced pressure
  4. filtrationThe resulting precipitate is filtered
  5. customdried under a vacuum

Sources & evidence

ORD record
ord-d89f17c38556498fb31364b19e20fc77
Source dataset
uspto-grants-1990_12
Patent number
US04980509

Reaction notes

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