Methanol → HCID 54185067, compound

HRID 261110Notes

Reaction equation

HRID 261110 reaction equation
S(=O)(=O)(O)O.S(O)(O)(=O)=O.[O:11]([C:18]1[CH:19]=[CH:20][C:21]2[CH2:22][C@H:23]3[N:34]([CH2:35][CH2:36][C:37]4[S:38][CH:39]=[CH:40][CH:41]=4)[CH2:33][CH2:32][C@@:29]4([C:30]=2[CH:31]=1)[C@H:24]3[CH2:25][CH2:26][CH2:27][CH2:28]4)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>CCOCC>[O:11]([C:18]1[CH:19]=[CH:20][C:21]2[CH2:22][C@H:23]3[N:34]([CH2:35][CH2:36][C:37]4[S:38][CH:39]=[CH:40][CH:41]=4)[CH2:33][CH2:32][C@@:29]4([C:30]=2[CH:31]=1)[C@H:24]3[CH2:25][CH2:26][CH2:27][CH2:28]4)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70582036HCID 70582036, compound

Product 1

HCID 54185067HCID 54185067, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The above base, 3.0 g. (0.007 mol) in ether was treated with sulfuric acid. The crude sulfate was recrystallized from methanol-ether to give 1.8 g. (49%) of pure (-)-3-phenoxy-N-[2-(2-thienyl)ethyl]morphinan sulfate, m.p. 135°-138°, [α]D25 =-67.28° (c 1.00, MeOH).

Workup

  1. customThe crude sulfate was recrystallized from methanol-ether
  2. customto give 1.8 g

Sources & evidence

ORD record
ord-262dcab124344ab1a0c6e77cd3ec6f7e
Source dataset
uspto-grants-1979_08
Patent number
US04163853

Reaction notes

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