Sodium borohydride → HCID 68154423, compound

HRID 73643Notes

Reaction equation

HRID 73643 reaction equation
[O:1]1[C@H:10]2[C:5](=[CH:6][CH2:7][CH2:8][C@H:9]2[CH:11]=[O:12])[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[O:1]1[C@H:10]2[C:5](=[CH:6][CH2:7][CH2:8][C@H:9]2[CH2:11][OH:12])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86668663HCID 86668663, compound

Product 1

HCID 68154423HCID 68154423, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

202 mg (8R,8aR)-3,4,6,7,8,8a-hexahydro-2H-chromene-8-carbaldehyde was dissolved in 8 mL MeOH and the solution was cooled to 0° C. and 52 mg sodium borohydride was added slowly. The reaction was stirred for several hours and gradually warmed to RT. The methanol was removed using a rotovap and the residue was diluted with CH2Cl2 and added to sat. NH4Cl. The mixture was separated, and the aqueous was extracted with CH2Cl2. The crude extract was dried over Na2SO4, filtered, concentrated, then purified on silica gel to provide the title compound. 1H NMR (400 MHz, CDCl3) δ=1.46-1.80 (m, 4H), 1.84-2.10 (m, 3H), 2.13-2.38 (m, 2H), 2.78-2.86 (m, 1H), 3.52-3.62 (m, 1H), 3.66-3.76 (m, 1H), 3.76-3.87 (m, 1H), 3.94-3.47 (m, 2H), 5.52 (s, 1H) ppm.

Workup

  1. temperaturegradually warmed to RT
  2. customThe methanol was removed
  3. additionthe residue was diluted with CH2Cl2
  4. additionadded to sat. NH4Cl
  5. customThe mixture was separated
  6. extractionthe aqueous was extracted with CH2Cl2
  7. extractionThe crude extract
  8. dry with materialwas dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified on silica gel

Sources & evidence

ORD record
ord-cc2ce523b11045a4a6f47a1b72679486
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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