HCID 70581408, compound → HCID 22808438, compound

HRID 261107Notes

Reaction equation

HRID 261107 reaction equation
Cl.[O:2]([C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:25]([CH2:26][CH:27]4[CH2:30][CH2:29][CH2:28]4)[CH2:24][CH2:23][C@@:20]4([C:21]=2[CH:22]=1)[C@H:15]3[CH2:16][CH2:17][CH2:18][CH2:19]4)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[O:2]([C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:25]([CH2:26][CH:27]4[CH2:30][CH2:29][CH2:28]4)[CH2:24][CH2:23][C@@:20]4([C:21]=2[CH:22]=1)[C@H:15]3[CH2:16][CH2:17][CH2:18][CH2:19]4)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 70581408HCID 70581408, compound

Product 1

HCID 22808438HCID 22808438, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above base, 1.1 g. (0.003 mol), on treatment with hydrogen chloride (anhydrous) in ethyl acetate, afforded the crude hydrochloride which after crystallization from ethyl acetate gave 1.2 g. (100%) of pure (-)-3-phenoxy-N-cyclobutylmethylmorphinan hydrochloride, m.p. 175°-177°, [α]D25 =-66.59° (c 1.03, MeOH).

Workup

  1. customafter crystallization from ethyl acetate
  2. customgave 1.2 g

Sources & evidence

ORD record
ord-da30ecba1de24124b1bf29c5a73bb780
Source dataset
uspto-grants-1979_08
Patent number
US04163853

Reaction notes

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