Ethanol → HCID 69817892, compound

HRID 2417420Notes

Reaction equation

HRID 2417420 reaction equation
[CH2:1]([N:8]([C@@H:28]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][CH:33]=1)[CH2:29][OH:30])[CH2:9][C@H:10]([OH:27])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O1CCOCC1.[Cl-].[NH4+]>[Fe].O>[NH2:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][C@H:28]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][C@H:10]([OH:27])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:15][CH:14]=2)[CH2:29][OH:30])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 25517Ammonium ChlorideHCID 312751,4-DioxaneHCID 69818222HCID 69818222, compound

Product 1

HCID 69817892HCID 69817892, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A solution of (2S)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]amino]-3-(4-nitrophenyl)-1-propanol (2.00 g) in a mixed solvent of ethanol (7.5 ml) and 1,4-dioxane (7.5 ml) was added dropwise to a stirred suspension of iron powder (2.00 g) and ammonium chloride (0.24 g) in a mixed solvent of ethanol (5 ml) and water (5 ml) at 85° C. over 10 minutes and the resulting mixture was stirred at the same temperature for 30 minutes. The insoluble solid was filtered off and washed with dioxane, and the filtrate was concentrated in vacuo. The residue was partitioned between saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated to give (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]-amino]-1-propanol (1.90 g) as a pale yellow oil.

Workup

  1. filtrationThe insoluble solid was filtered off
  2. washwashed with dioxane
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between saturated aqueous sodium hydrogencarbonate solution and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-b58a85fb0a714c68b42283888b251703
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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