Ethyl chloroformate → 2-Benzyl-5-carbethoxy-2,5-diazabicyclo[2.2.1]heptane

HRID 268231Notes

Reaction equation

HRID 268231 reaction equation
Cl.C(N1CC2CC1CN2C(=O)N(CC)CC)C1C=CC=CC=1.I.I.[CH2:25]([N:32]1[CH2:37][CH:36]2[CH2:38][CH:33]1[CH2:34][NH:35]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl[C:40]([O:42][CH2:43][CH3:44])=[O:41]>>[CH2:25]([N:32]1[CH2:37][CH:36]2[CH2:38][CH:33]1[CH2:34][N:35]2[C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 215454962-benzyl-5-(N,N-diethyl-carbamyl)2,5-diazabicyclo[2.2.1]heptane hydrochlorideHCID 224039562-Benzyl-2,5-diazabicyclo[2.2.1]heptane dihydroiodide

Product 1

HCID 220995342-Benzyl-5-carbethoxy-2,5-diazabicyclo[2.2.1]heptaneYield 68%

Procedure

Using the procedure for preparation of 2-benzyl-5-(N,N-diethylcarbamyl)-2,5-diazabicyclo[2.2.1]heptane hydrochloride as related in Example 11, 29.0 g of 2-benzyl-2,5-diazabicyclo[2.2.1]heptane dihydroiodide, prepared according to the procedure given in Example 11, was treated with 1.5 equivalents of ethyl chloroformate to yield crude product. Dry column chromatography, a technique described by B. Loev and M. M. Goodman in Chem. Ind. (London), p 2026, 1967, on 1700 g alumina using chloroform development provided 11.6 g (68%) of pure product, characterized as the maleate salt, melting point 124°-128° C.

Workup

  1. customprepared
  2. customto yield crude product
  3. customDry column chromatography

Sources & evidence

ORD record
ord-da63c3ee39cd40f5a28e404e0965ea10
Source dataset
uspto-grants-1976_03
Patent number
US03947445

Reaction notes

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