(R)-t-butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate → (R)-1-[3-(2-pyrrolidinyl)-2-propynyl]pyrrolidine

HRID 846663Notes

Reaction equation

HRID 846663 reaction equation
[N:1]1([CH2:6][C:7]#[C:8][C@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2C(OC(C)(C)C)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[NH:10]1[CH2:11][CH2:12][CH2:13][C@@H:9]1[C:8]#[C:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 9860463(R)-t-butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate

Product 1

HCID 14730289(R)-1-[3-(2-pyrrolidinyl)-2-propynyl]pyrrolidineYield 136.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(R)-t-Butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate (11.06 g, 0.039 mol) was dissolved in methanolic HCl (200 mL) and stirred at room temperature for 2 hr. The reaction was evaporated under house and high vacuum to give a beige solid which was recrystallized from methanol:ether to give 9.5 g of product. The analytical sample was recrystallized from methanol:ether; m.p. 214°-216° C. [α]D +21° (c 0.55, MeOH).

Workup

  1. customThe reaction was evaporated under house and high vacuum
  2. customto give a beige solid which
  3. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-74f208c995794f21879eee883b016125
Source dataset
uspto-grants-1992_08
Patent number
US05137905

Reaction notes

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