Phosphate → (R)-N,N-diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine

HRID 428317Notes

Reaction equation

HRID 428317 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C(O)(=O)C(C1C=CC=CC=1)O.[CH:26]([N:29]([CH:48]([CH3:50])[CH3:49])[CH2:30][CH2:31][C@@H:32]([C:39]1[CH:44]=[C:43]([CH2:45][OH:46])[CH:42]=[CH:41][C:40]=1[OH:47])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:28])[CH3:27].P([O-])([O-])([O-])=O.[OH-].[Na+]>C(OCC)C.ClCCl>[CH:48]([N:29]([CH:26]([CH3:28])[CH3:27])[CH2:30][CH2:31][C@@H:32]([C:39]1[CH:44]=[C:43]([CH:45]=[O:46])[CH:42]=[CH:41][C:40]=1[OH:47])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:50])[CH3:49]

Participants

7

Reactant 4

HCID 1061PhosphateHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 69343213(R)-N,N-diisopropyl-3-(2-hydroxy-5-hydroxymethylphenyl)-3-phenylpropanamine mandelate

Product 1

HCID 53380832(R)-N,N-diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

DDQ (1.1 eq) was added to a solution of (R)-N,N-diisopropyl-3-(2-hydroxy-5-hydroxymethylphenyl)-3-phenylpropanamine mandelate (prepared as described in WO 94/11337, Example 1) (2.46 g, 5 mmol), dichloromethane (20 mL) and phosphate buffer (pH 7) (0.1 mL). Thereafter, sodium hydroxide solution (20 mL, 1 M) and diethyl ether were added and the phases were separated. The water-phase was extracted twice with dichloromethane-diethyl ether (2:1). The organic phase was dried (MgSO4) and evaporated. The residue was crystallised from ethyl acetate-hexane to yield 1.35 g (80%).

Workup

  1. customthe phases were separated
  2. extractionThe water-phase was extracted twice with dichloromethane-diethyl ether (2:1)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe residue was crystallised from ethyl acetate-hexane
  6. customto yield 1.35 g (80%)

Sources & evidence

ORD record
ord-2a05ebd6ff974fb7a59d5a7b8fea72f0
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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