Hydrochloric Acid → HCID 9909516, compound

HRID 346119Notes

Reaction equation

HRID 346119 reaction equation
[OH:1][C@@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:4]([C@@H:5]([F:29])[C:6](=[O:28])[C@@H:7]3[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:27])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1.[BH4-].[Na+].O.Cl>O1CCCC1.CO.C(OCC)(=O)C>[OH:1][C@@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:4]([C@@H:5]([F:29])[C@H:6]([OH:28])[C@@H:7]3[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:27])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 18647598HCID 18647598, compound

Product 1

HCID 9909516HCID 9909516, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3α-hydroxy-6α-fluoro-7-keto-5β-cholanoic acid (0.42 g, 1.02 mmoles) in tetrahydrofuran (44 ml) was added with sodium borohydride (0.165 g, 4.36 mmoles) in methanol (11 ml) and the resulting mixture was left to react for one hour under magnetic stirring. Then the reaction mixture was diluted with ethyl acetate (20 ml), added with water (20 ml) and acidified with 10% hydrochloric acid (10 ml). The organic phase was separated, the aqueous phase was extracted with methylene chloride (3×20 ml); the combined organic phases were washed with brine (1×30 ml) and dried over sodium sulfate. After evaporating the solvent, the residue (0.42 g) was subjected to flash chromatography on silica, eluting with methylene chloride/methanol 98:2, to obtain 0.03 g of the starting product and 0.16 g of the title product (41%), the structure of which was confirmed by 1H-NMR, 13C-NMR, 19F-NMR and mass spectroscopies. mp 198-201° C.; IR (CHCl3) 1725 (C=O); 1H-NMR (200 MHz, CDCl3 +CD3OD) 0.7 (s, 3H, 18-CH3), 0.9-0.95 (m, 6H, 19-CH3, 21-CH3), 3.38 (m, 1H, 6-H), 3.7 (m, 2H, 3H, 7-H); 13C-NMR (200 MHz, CDCl3 +CD3OD) 75.43 C3, 79.199 C7, 95.45 C6. 176.24 (--COOH); 19F-NMR(CDCl3 +CD3OD) inner standard C6F6, φ-5.4; m/z 391 (9.18%), 390 (34.28%), 354.4 (2.64%). C24H39OF4.

Workup

  1. waitthe resulting mixture was left
  2. customto react for one hour under magnetic stirring
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with methylene chloride (3×20 ml)
  5. washthe combined organic phases were washed with brine (1×30 ml)
  6. dry with materialdried over sodium sulfate
  7. customAfter evaporating the solvent
  8. washeluting with methylene chloride/methanol 98:2

Sources & evidence

ORD record
ord-10921661087b460786b7b5f9447f57a8
Source dataset
uspto-grants-1991_10
Patent number
US05061701

Reaction notes

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