Sodium Hydroxide → (R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

HRID 1473004Notes

Reaction equation

HRID 1473004 reaction equation
C1(C)C=CC([C@]([C@H](C(O)=O)O)(O)C(O)=O)=CC=1.[CH:18]([N:21]([CH2:25][CH2:26][CH:27]([C:34]1[CH:39]=[C:38]([Br:40])[CH:37]=[CH:36][C:35]=1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19].[OH-].[Na+]>O>[CH:18]([N:21]([CH2:25][CH2:26][C@@H:27]([C:34]1[CH:39]=[C:38]([Br:40])[CH:37]=[CH:36][C:35]=1[O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:22]([CH3:24])[CH3:23])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 129724153-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amineHCID 86691363HCID 86691363, compound

Product 1

HCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the obtained p-toluyl-L-tartaric acid salt of N,N-Diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine of formula (E) added 500 ml R.O. Water and 300 ml MDC reaction cooled to 0° C. to 5° C. and pH was adjusted at 9 to 10 by 10% sodium hydroxide followed by raising of temperature to 25° C. to 35° C. Layers were separated and MDC layer washed with 2×200 ml 20% brine solution and finally MDC was distilled out under vacuum below 50° C. to afford title compound (R)—N,N-Diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-Phenylpropylamine compound of formula (F).

Workup

  1. temperaturecooled to 0° C. to 5° C.
  2. temperatureby raising of temperature to 25° C. to 35° C
  3. customLayers were separated
  4. washMDC layer washed with 2×200 ml 20% brine solution and finally MDC
  5. distillationwas distilled out under vacuum below 50° C.

Sources & evidence

ORD record
ord-1a20e5639eed4a6c80ecd50c2ec1eb3b
Source dataset
uspto-grants-2015_04
Patent number
US09012678B2

Reaction notes

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