Sodium borohydride → HCID 21450364, compound

HRID 1657462Notes

Reaction equation

HRID 1657462 reaction equation
[Br-].[CH3:2][C:3]1([CH3:37])[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][N+:16]([CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)=[CH:15][CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:8][C:9]=2[O:30][CH3:31])[O:4]1.[BH4-].[Na+]>C(O)C.O.C(OCC)C>[CH3:2][C:3]1([CH3:37])[CH2:12][CH:11]([C:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[CH2:15][CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:8][C:9]=2[O:30][CH3:31])[O:4]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 131710266HCID 131710266, compound

Product 1

HCID 21450364HCID 21450364, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

This pyridinium bromide (5.86g.) was dissolved in a mixture of ethanol (70 ml.) and water (23 ml.) and sodium borohydride (0.74g.) was added portionwise to the stirred solution at ambient temperature. At the end of the addition, the solution was stirred for a further 0.5 hours and was then diluted with diethyl ether (300 ml.) and water (300 ml.). The organic layer was separated, dried over anhydrous potassium carbonate and evaporated under reduced pressure. The residual amber gum (4.96g.) was purified via column chromatography on silica gel using 60°-80° petroleum ether/ethyl acetate mixtures as eluent to give 2,2-Dimethyl-5-methoxy-4-[1-(2-naphthylmethyl)-1,2,5,6-tetrahydropyrid-4-yl]-7-n-pentylchroman as an orange oil (2.70g.).

Workup

  1. additionwas added portionwise to the stirred solution at ambient temperature
  2. additionAt the end of the addition
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous potassium carbonate
  5. customevaporated under reduced pressure
  6. customThe residual amber gum (4.96g.) was purified via column chromatography on silica gel using 60°-80° petroleum ether/ethyl acetate mixtures as eluent

Sources & evidence

ORD record
ord-6086300b163c4aa89146be4e0c7421a5
Source dataset
uspto-grants-1976_06
Patent number
US03960880

Reaction notes

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