Tetrafluoro-m-phenylenediamine dihydrochloride → (S)-1-[3-(2-pyrrolidinyl)-2-propynyl]pyrrolidine

HRID 846664Notes

Reaction equation

HRID 846664 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.N1(C([O-])=O)CCCC1.[N:23]1([CH2:28][C:29]#[C:30][C@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2C(OC(C)(C)C)=O)[CH2:27][CH2:26][CH2:25][CH2:24]1>CO>[NH:32]1[CH2:33][CH2:34][CH2:35][C@H:31]1[C:30]#[C:29][CH2:28][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 9860463(R)-t-butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylateHCID 223251731-Pyrrolidinecarboxylate

Product 1

HCID 14730290(S)-1-[3-(2-pyrrolidinyl)-2-propynyl]pyrrolidineYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was obtained as the dihydrochloride salt following Example 50, Part A by substituting (S)-t-butyl (1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate for (R)-t-butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate, a white hygroscopic powder, m.p. 208°-211° C. [a]D -23° (c 0.75, MeOH). Recrystallization of the mother liquor gave an additional 26% of product.

Workup

  1. customRecrystallization of the mother liquor

Sources & evidence

ORD record
ord-5e162bc6e4b849dc90cb0670aef86f49
Source dataset
uspto-grants-1992_08
Patent number
US05137905

Reaction notes

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