Pyrrolidine → 1-[(1,4-Dioxa-8-azaspiro[4.5]dec-7-yl)carbonyl]pyrrolidine

HRID 1196507Notes

Reaction equation

HRID 1196507 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH:7]([C:11]([O:13]C)=O)[CH2:6]2)[O:4][CH2:3][CH2:2]1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[O:4]1[C:5]2([CH2:10][CH2:9][NH:8][CH:7]([C:11]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:13])[CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 15123245Methyl 1,4-dioxa-8-azaspiro[4.5]decane-7-carboxylate

Product 1

HCID 151232461-[(1,4-Dioxa-8-azaspiro[4.5]dec-7-yl)carbonyl]pyrrolidine

Conditions

Temperature
150 °C

Procedure

A mixture of the product of stage (iv) (0.887 g) and pyrrolidine (2.2 ml) was heated at 150° C. in an autoclave for 2 h, allowed to cool to room temperature and evaporated to dryness giving an oil (1.27 g). This was purified by flash chromatography eluting with chloroformmethanol (9:1), to give an oil which crystallised on standing to give the title compound as a solid (841 mg), m.p. 72.5°-74.5°.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-a10b588e6bb34bf49322b92de65c53e0
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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