Ethyl chloroformate → ethyl 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4-carbamate

HRID 2398816Notes

Reaction equation

HRID 2398816 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]21[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]2.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>N1C=CC=CC=1>[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]21[CH2:12][CH2:13][CH:14]([NH:17][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:16]2

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 122512743',4'-Dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride

Product 1

HCID 21433573ethyl 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4-carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice cooled solution of the free base prepared from 1.5 g. of 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride [I(c)] (prepared as in Example 10C) in 12 ml. of pyridine, 1 ml. of ethyl chloroformate is added. The mixture is allowed to stand in the cold for about 5 hours and then poured into ice water. The solid that precipitates is collected on a filter and recrystallized from methylene chloride: benzene to give ethyl 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalene]-4-carbamate [I(c)].

Workup

  1. customcold for about 5 hours
  2. customThe solid that precipitates
  3. customis collected on
  4. filtrationa filter
  5. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-90622c0909964f818d98d38cc76b1dd5
Source dataset
uspto-grants-1977_05
Patent number
US04025558

Reaction notes

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