Tetrahydrofuran → (S)-N-benzyloxycarbonyl-3-carbamoyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline

HRID 618687Notes

Reaction equation

HRID 618687 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:20]([CH2:21][OH:22])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[OH-:35].[NH4+:36].[O:37]1[CH2:41]CCC1>>[CH2:1]([O:8][C:9]([N:11]1[C@H:20]([C:21]([O:35][C:41](=[O:37])[NH2:36])=[O:22])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 12114557benzyl (3S)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 86754510(S)-N-benzyloxycarbonyl-3-carbamoyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline

Procedure

To (S)-N-benzyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline(1 g) in tetrahydrofuran (5 mL) was added carbonyl diimidazole (0.6 g) and stirred for 45 minutes. Ammonium hydroxide (30%, 5 mL) was added and after overnight stirring, the reaction mixture was extracted with ethyl acetate. The extract was washed with water, 0.5 N HCl, concentrated and recrystallized from ethanol to yield the product as a white solid (0.67 g). Melting point 136.0-137.9° C.

Workup

  1. stirringstirring
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with water, 0.5 N HCl
  4. concentrationconcentrated
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f85c27230b164099bc2f51e19893a6f8
Source dataset
uspto-grants-1999_09
Patent number
US05955471

Reaction notes

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