Methanol → HCID 53904405, compound

HRID 261108Notes

Reaction equation

HRID 261108 reaction equation
C(O)(=O)C(O)=O.C(O)(=O)C(O)=O.[O:13]([C:20]1[CH:21]=[CH:22][C:23]2[CH2:24][C@H:25]3[N:36]([CH2:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH2:35][CH2:34][C@@:31]4([C:32]=2[CH:33]=1)[C@H:26]3[CH2:27][CH2:28][CH2:29][CH2:30]4)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO>CCOCC>[O:13]([C:20]1[CH:21]=[CH:22][C:23]2[CH2:24][C@H:25]3[N:36]([CH2:37][CH2:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH2:35][CH2:34][C@@:31]4([C:32]=2[CH:33]=1)[C@H:26]3[CH2:27][CH2:28][CH2:29][CH2:30]4)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 971Oxalic AcidHCID 70582054HCID 70582054, compound

Product 1

HCID 53904405HCID 53904405, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the above base, 3.2 g. (0.007 mol) in ether, a solution of 0.8 g. of oxalic acid in ether was added. The crude oxalate was recrystallized twice from ethanol to give 1.7 g. (39%) of pure (-)-3-phenoxy-N-phenethylmorphinan oxalate, m.p. 217°-219°, [α]D25 =-72.17° (c 1.06, MeOH).

Workup

  1. customThe crude oxalate was recrystallized twice from ethanol
  2. customto give 1.7 g

Sources & evidence

ORD record
ord-eeac4031bacc4a70ac6301f449b989bb
Source dataset
uspto-grants-1979_08
Patent number
US04163853

Reaction notes

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