Sodium borohydride → HCID 86753365, compound

HRID 357262Notes

Reaction equation

HRID 357262 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([OH:22])[CH2:18][NH:19][CH2:20][CH3:21])=[CH:16][C:3]1=2.[BH4-].[Na+]>CO>[OH:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([OH:22])[CH2:18][NH:19][CH2:20][CH3:21])=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67797526HCID 67797526, compound

Product 1

HCID 86753365HCID 86753365, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)-N-ethyl-N-hydroxyethylamine (4.1 g) in 100 ml methanol at 0° C. was treated with sodium borohydride (1.04 g) in two portions and stirred under a nitrogen blanket for 2 hours. The solution was evaporated and taken up in chloroform and washed with saturated bicarbonate. This solution was evaporated again and the residue purified by flash chromatography (silica gel, 19:1 Chloroform-methanol) to give an oil. This oil crystallized from ether to give 2.7 g of 2-(6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-yl)-N-ethyl-N-hydroxyethylamine, as crystals, m.p. 116°-118° C.

Workup

  1. customThe solution was evaporated
  2. washwashed with saturated bicarbonate
  3. customThis solution was evaporated again
  4. customthe residue purified by flash chromatography (silica gel, 19:1 Chloroform-methanol)
  5. customto give an oil
  6. customThis oil crystallized from ether

Sources & evidence

ORD record
ord-a59346651ddb4819b63e8c17873798e6
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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