Triethylamine → (+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

HRID 1937363Notes

Reaction equation

HRID 1937363 reaction equation
[N:1]1([C:6]([NH2:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[C:24]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:25]([NH:27][C@@H:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35](N)[CH:36]=2)[CH2:31][CH2:30][C@H:29]1[O:39][C:40](=[O:42])[CH3:41])=[O:26]>C(Cl)Cl>[Cl:21][C:22]1[CH:23]=[C:24]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:25]([NH:27][C@@H:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH:8][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:36]=2)[CH2:31][CH2:30][C@H:29]1[O:39][C:40](=[O:42])[CH3:41])=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1383351-PyrrolidinecarboxamideHCID 12042344(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-aminotetraline

Product 1

HCID 21338527(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of pyrrolidine carboxamide (1.5 mL) in CH2Cl2 (25 mL) was treated with POCl3 (0.23 mL). After 1.5 h, the solution was treated with triethylamine (1 mL) and 115 (0.5 g). After stirring over night, the solvent was evaporated, the residue was treated with ice-water, the mixture neutralized, and the mixture extracted with EtOAc. The extracts were washed with brine and the solvent was dried and evaporated to give a dark oil. The oil was purified by radial chromatography eluting with 5% EtOH—CHCl3 to give a tan solid that was recrystallized from EtOAc to give a white solid (0.18 g), m.p. 229° C., dec.

Workup

  1. customthe solvent was evaporated
  2. additionthe residue was treated with ice-water
  3. extractionthe mixture extracted with EtOAc
  4. washThe extracts were washed with brine
  5. customthe solvent was dried
  6. customevaporated
  7. customto give a dark oil
  8. customThe oil was purified by radial chromatography
  9. washeluting with 5% EtOH—CHCl3
  10. customto give a tan solid
  11. customthat was recrystallized from EtOAc

Sources & evidence

ORD record
ord-deb14e7de62a43b79125e5a8db72658f
Source dataset
uspto-grants-2002_05
Patent number
US06395735B2

Reaction notes

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