HCID 70581408, compound → HCID 22808438, compound

HRID 1763867Notes

Reaction equation

HRID 1763867 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-fa9413b1c2c841c49c1ca7562022ca77
Source dataset
uspto-grants-1978_09
Patent number
US04113729

Reaction notes

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