Pyrrolidine → HCID 71548309, compound

HRID 512928Notes

Reaction equation

HRID 512928 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]4[O:26][C:25](=[O:27])[C:24]5[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=5[CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]([OH:26])[CH2:21][CH2:22][C:23]4[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=4[C:25]([N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:27])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 25160788HCID 25160788, compound

Product 1

HCID 71548309HCID 71548309, compoundYield 61.6%

Procedure

A stirred solution of lactone 49 (21.0 g, 49.0 mmol) in pyrrolidine (20 ml, 241 mmol) was heated at 90° C. for 3 hours. Excess pyrrolidine was distilled off and the residue was dissolved in dichloromethane (200 ml) followed by FC to give desired hydroxy pyrrolidinamide 50 (15.0 g, 61%) as a pale yellow solid.

Workup

  1. distillationExcess pyrrolidine was distilled off
  2. dissolutionthe residue was dissolved in dichloromethane (200 ml)

Sources & evidence

ORD record
ord-ac22e9426e63438da4e7c1c004294d7c
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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