Sodium borohydride → HCID 68807529, compound

HRID 411281Notes

Reaction equation

HRID 411281 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([C@@:11]23[CH2:20][C@H:15]([CH2:16][C:17](=[O:19])[CH2:18]2)[N:14]([CH3:21])[CH2:13][C@H:12]3[CH3:22])[CH:8]=[CH:9][CH:10]=1)[CH3:3].[BH4-].[Na+]>C(O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([C@@:11]23[CH2:20][C@H:15]([CH2:16][CH:17]([OH:19])[CH2:18]2)[N:14]([CH3:21])[CH2:13][C@H:12]3[CH3:22])[CH:8]=[CH:9][CH:10]=1)[CH3:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68807523HCID 68807523, compound

Product 1

HCID 68807529HCID 68807529, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 15 (1 eq) dissolved in absolute ethanol (7 mL/g of 15) was added solid sodium borohydride slowly over 10 minutes. This mixture was allowed to stir at room temperature for 24 hours after which time the ethanol was removed under aspirator vacuum and the residue carefully dissolved in 0.5N HCl (6 mL/g of 15). This solution was washed twice with ether (3 mL/g of 15 for each wash) and then the aqueous solution is made basic with 50% NaOH solution (pH=14) and the ether layers discarded. This solution was then saturated with sodium chloride and extracted five times with 3:1, methylene chloride:THF, (3 mL/g of 15 for each extraction) and the combined organic layers were dried over magnesium sulfate and the solvent removed under aspirator vacuum to provide 16 as a yellow oil in 95% yield from 15 as a mixture of 7-hydroxy diastereomers. This material is used in the next step without purification. 1H NMR (CDCl3): δ0.46-0.48(d, J=6.90 Hz, 3H), 1.32-1.34 (d, J=6.02 Hz, 6H), 1.47-1.58(m, 2H), 1.87-1.93(dd, J=14.16, 5.09 Hz, 2H), 2.27-2.47 (m, 8H), 2.69-2.75 (dd, J=11.64, 5.26 Hz, 1H), 3.09 (br s, 1H), 4.02-4.05 (t, J=4.83 Hz, 1H), 4.47-4.59 (septet, J=6.07 Hz, 1H)5.30 (br s, 1H), 6.68-6.81 (m, 3H), 7.7.16-7.62 (in, 1H).

Workup

  1. customwas removed under aspirator vacuum
  2. dissolutionthe residue carefully dissolved in 0.5N HCl (6 mL/g of 15)
  3. washThis solution was washed twice with ether (3 mL/g of 15 for
  4. washeach wash) and then the aqueous solution
  5. extractionsaturated with sodium chloride and extracted five times with 3:1, methylene chloride
  6. extractionTHF, (3 mL/g of 15 for each extraction) and the combined organic layers
  7. dry with materialwere dried over magnesium sulfate
  8. customthe solvent removed under aspirator vacuum

Sources & evidence

ORD record
ord-29f4b74e75964e6bbd4267c29c0b1ac2
Source dataset
uspto-grants-2003_05
Patent number
US06559159B2

Reaction notes

Loading…