Methanol → HCID 54469216, compound

HRID 1763869Notes

Reaction equation

HRID 1763869 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[O:40][CH:41]=[CH:42][CH:43]=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[O:40][CH:41]=[CH:42][CH:43]=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 70582160HCID 70582160, compound

Product 1

HCID 54469216HCID 54469216, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the above base, 1.2 g. (0.003 mol) in ether, a solution of 0.3 g. of oxalic acid in ether was added. The crude oxalate was recrystallized twice from ethanol to give 1.0 g. (68%) of (-)-3-phenoxy-N-[2-(2-furyl)ethyl]morphinan oxalate, m.p. 195°-197° (d), [α]D25 = -64.52° (c 1.03, MeOH).

Workup

  1. customThe crude oxalate was recrystallized twice from ethanol
  2. customto give 1.0 g

Sources & evidence

ORD record
ord-f57cecbbd284475dbffa30a6175cd8d0
Source dataset
uspto-grants-1978_09
Patent number
US04113729

Reaction notes

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