Water → 1-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-nitro-phenoxy)-2-propanol

HRID 1391050Notes

Reaction equation

HRID 1391050 reaction equation
C([O:4][C:5]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:6]=1[O:7][CH2:8][CH:9]([OH:23])[CH2:10][N:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C=C.O.C(N(CC)CC)C>C(O)C.[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Rh+3].[Cl-].[Cl-]>[CH2:12]([N:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:10][CH:9]([OH:23])[CH2:8][O:7][C:6]1[CH:24]=[CH:25][CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[C:5]=1[OH:4])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 572310521-(2-allyloxy-3-nitro-phenoxy)-3-(N-benzyl-tert.-butylamino)-2-propanol

Product 1

HCID 570217691-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-nitro-phenoxy)-2-propanol

Reagents, catalysts & solvents 2

HCID 21948325Rhodium tris(triphenylphosphine)chlorideCatalystHCID 702EthanolSolvent

Procedure

A solution of 19.4 g of 1-(2-allyloxy-3-nitro-phenoxy)-3-(N-benzyl-tert.-butylamino)-2-propanol in a mixture of 350 ml of ethanol, 35 ml of water and 5 ml of triethylamine, with the addition of 1 g of rhodium tris-(triphenylphosphine)-chloride, is stirred under reflux for 45 minutes. After filtering and evaporating the filtrate, crude 1-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-nitro-phenoxy)-2-propanol is obtained in the form of a dark red oil, which is used further without further purification.

Workup

  1. temperatureunder reflux for 45 minutes
  2. filtrationAfter filtering
  3. customevaporating the filtrate

Sources & evidence

ORD record
ord-dfec8dded184410c8791e0343ab4110b
Source dataset
uspto-grants-1979_02
Patent number
US04140789

Reaction notes

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