Methanol → HCID 25168568, compound

HRID 1175302Notes

Reaction equation

HRID 1175302 reaction equation
[Cl:1][C:2]1[C:3]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=2)=[CH:4][C:5]([C@H:14]2[C@H:19]([OH:20])[C@@H:18]([OH:21])[C@H:17]([OH:22])[C@@H:16]([CH2:23][OH:24])[O:15]2)=[C:6]([CH:13]=1)[CH2:7][O:8][CH2:9][C:10](=[O:12])[CH3:11].[BH4-].[Na+].CO>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:32][CH3:33])=[CH:30][CH:31]=2)=[CH:4][C:5]([C@H:14]2[C@H:19]([OH:20])[C@@H:18]([OH:21])[C@H:17]([OH:22])[C@@H:16]([CH2:23][OH:24])[O:15]2)=[C:6]([CH2:7][O:8][CH2:9][CH:10]([OH:12])[CH3:11])[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 25168566HCID 25168566, compound2×

Product 1

HCID 25168568HCID 25168568, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-chloro-4-(4-ethylbenzyl)-2-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)propan-2-one (compound K) (3.7 mg, 0.0077 mmol) in dry THF (0.5 mL) was added NaBH4 (1.76 mg, 0.0045 mmol) with stirring under argon at room temperature. After the mixture was stirred for 20 min, anhydrous methanol was added dropwise, and the resulting mixture was stirred at 20° C. for 2 h, then quenched by addition of sat. NH4Cl. The mixture was extracted with EtOAc and the combined organic layers were washed with water, brine, dried over Na2SO4, filtered and concentrated to provide the crude product, which was purified by preparative TLC to yield 2.5 mg of the product. 1H-NMR (CD3OD, 300 MHz) δ 7.45 (s, 1H), 7.43 (s, 1H), 7.08 (s, 4H), 4.75-4.56 (m, 1H), 4.47 (dd, J=9.3 Hz, 3.3 Hz, 1H), 4.10 (d, J=14.8 Hz, 1H), 4.05 (d, J=14.8 Hz, 1H), 3.93-3.83 (m, 2H), 3.68-3.66 (m, 1H), 3.47-3.37 (m, 6H), 2.60 (q, J=7.8 Hz, 2H), 1.21 (t, J=7.8 Hz, 3H), 1.15 (d, J=7.8 Hz, 3H); LC-MS (m/z) 481 [(M+1)+], 525 [(M+45)−].

Workup

  1. stirringAfter the mixture was stirred for 20 min
  2. stirringthe resulting mixture was stirred at 20° C. for 2 h
  3. customquenched by addition of sat. NH4Cl
  4. extractionThe mixture was extracted with EtOAc
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto provide the crude product, which
  10. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-30dc13f6d4ba4fc48b9bb4f71e1b20b7
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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