Isopropanol → HCID 19029767, compound

HRID 2256349Notes

Reaction equation

HRID 2256349 reaction equation
[N:1]1([NH:7][C:8](=[O:34])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([C:19]3[CH:28]=[CH:27][C:26]4[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=4[CH:20]=3)=[O:18])=[CH:11][C:10]=2[OH:33])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C)C.C1COCC1.[BH4-].[Na+]>CC(C)=O>[N:1]1([NH:7][C:8](=[O:34])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]([OH:18])[C:19]3[CH:28]=[CH:27][C:26]4[C:25]([CH3:29])([CH3:30])[CH2:24][CH2:23][C:22]([CH3:31])([CH3:32])[C:21]=4[CH:20]=3)=[CH:11][C:10]=2[OH:33])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21474566HCID 21474566, compound

Product 1

HCID 19029767HCID 19029767, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

3.43 g (7.6 mmol) of N-piperidinyl-2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl-methoxy)benzamide, 100 ml of isopropanol and 50 ml of THF are introduced into a flask. The mixture is cooled to 0° C. and 144 mg (3.81 mmol) of NaBH4 are added. The mixture is stirred at 0° C. for 1 hour. Acetone is added, the solvents are evaporated, the residue is taken up in water and the mixture is adjusted to pH 6-7 with hydrochloric acid (1N). The mixture is extracted with ethyl acetate, washed with water and dried over sodium sulphate, and the solvents are evaporated. The residue obtained is purified by chromatography on a silica column eluted with a mixture of ethyl acetate and hexane (35:65). After evaporation of the solvents, the oil obtained is crystallised in hexane, filtered and dried, and 4.25 g (86%) of the expected product of melting point 124° C. are collected.

Workup

  1. customthe solvents are evaporated
  2. extractionThe mixture is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customthe solvents are evaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a mixture of ethyl acetate and hexane (35:65)
  9. customAfter evaporation of the solvents
  10. customthe oil obtained
  11. customis crystallised in hexane
  12. filtrationfiltered
  13. customdried
  14. custom4.25 g (86%) of the expected product of melting point 124° C. are collected

Sources & evidence

ORD record
ord-e24b8cafc98342f3ad2f3ed625322921
Source dataset
uspto-grants-1997_08
Patent number
US05654331

Reaction notes

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