Ethanol → HCID 69817666, compound

HRID 2417410Notes

Reaction equation

HRID 2417410 reaction equation
[CH2:1]([N:8](C(O)CCC1C=CC([N+]([O-])=O)=CC=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[Cl-].[NH4+:35].[CH2:36]([OH:38])[CH3:37]>[Fe]>[NH2:35][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][C@H:37]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:36][OH:38])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 86591183HCID 86591183, compound

Product 1

HCID 69817666HCID 69817666, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a suspension of (2S)-2-[(N-benzyl-N-((2S)-2-hydroxy-3-phenoxypropyl]amino]-3-(4-nitrophenyl)-1-propanol (1.12 g) in ethanol (11 ml)—water (2.2 ml) were added powdered iron (573 mg) and ammonium chloride (55 mg). The mixture was gently heated to reflux for 1 hour and allowed to cool to room temperature. After the insoluble material was filtered off, the filtrate was concentrated and partitioned between chloroform and water. The organic layer was separated, washed successively with water and brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-1-propanol (990 mg) as a pale yellow oil.

Workup

  1. temperatureThe mixture was gently heated
  2. temperatureto reflux for 1 hour
  3. filtrationAfter the insoluble material was filtered off
  4. concentrationthe filtrate was concentrated
  5. custompartitioned between chloroform and water
  6. customThe organic layer was separated
  7. washwashed successively with water and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-41d7adc3ff60447296ec2d93e77947da
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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