Water → HCID 14461332, compound

HRID 1086816Notes

Reaction equation

HRID 1086816 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH:13]=[CH:14][N+:15]([O-])=[O:16])=[C:11]([CH:18]([CH3:20])[CH3:19])[N:10]([CH:21]([CH3:23])[CH3:22])[C:9]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.B.O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][CH2:14][NH:15][OH:16])=[C:11]([CH:18]([CH3:19])[CH3:20])[N:10]([CH:21]([CH3:23])[CH3:22])[C:9]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 14798Sodium HydroxideHCID 54330746HCID 54330746, compound

Product 1

HCID 14461332HCID 14461332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 30 g (76.5 mmol) of the compound of example 5 in 200 ml of warm tetrahydrofuran is added dropwise to 19.1 ml (0.19 mol) of a 1N solution of borane acid in tetrahydrofuran at 0° C. under an argon atmosphere; 0.5 g (13.2 mmol) of sodium hydridoborate are then added and the mixture is stirred for 2 h at room temperature. Then 180 ml of cold water are added dropwise with care and the mixture is boiled for 1 h under reflux. The mixture is adjusted to a pH of 13 with 10 ml of 6N sodium hydroxide solution, extracted three times, each time with 200 ml of ethyl acetate and the combined organic phases are dried over sodium sulphate and evaporated to dryness. The residue is chromatographed on 500 g of silica gel (230 to 400 mesh) with dichloromethane, dichloromethane/methanol (10:1) and dichloromethane/methanol/concentrated ammonia (100:10:1) until the main product emerges with the lowest Rf -value.

Workup

  1. waitthe mixture is boiled for 1 h
  2. temperatureunder reflux
  3. extractionextracted three times
  4. dry with materialeach time with 200 ml of ethyl acetate and the combined organic phases are dried over sodium sulphate
  5. customevaporated to dryness
  6. customThe residue is chromatographed on 500 g of silica gel (230 to 400 mesh) with dichloromethane, dichloromethane/methanol (10:1) and dichloromethane/methanol/concentrated ammonia (100:10:1) until the main product

Sources & evidence

ORD record
ord-20a19dfe64aa4c47af1d8db931da3f44
Source dataset
uspto-grants-1991_07
Patent number
US05032590

Reaction notes

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