5,6-Dibenzyl 7-(tert-butyl) (6S,7S)-5-azaspiro[2.5]octane-5,6,7-tricarboxylate → HCID 16108946, compound

HRID 1664601Notes

Reaction equation

HRID 1664601 reaction equation
[CH2:1]1[C:3]2([CH2:8][C@H:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@@H:6]([C:16]([O:18]CC3C=CC=CC=3)=[O:17])[N:5](C(OCC3C=CC=CC=3)=O)[CH2:4]2)[CH2:2]1.[H][H]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:12]([O:11][C:9]([C@H:7]1[CH2:8][C:3]2([CH2:1][CH2:2]2)[CH2:4][NH:5][C@@H:6]1[C:16]([OH:18])=[O:17])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 160695765,6-Dibenzyl 7-(tert-butyl) (6S,7S)-5-azaspiro[2.5]octane-5,6,7-tricarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 16108946HCID 16108946, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

5,6-dibenzyl 7-tert-butyl (6S,7S)-5-azaspiro[2.5]octane-5,6,7-tricarboxylate (2.0 g) was hydrogenated in methanol (100 mL) with 5% Pd—BaSO4 (750 mg) under a hydrogen atmosphere (hydrogen-balloon) at RT. The catalyst was removed by filtration. The filtrate was concentrated. The residue was dried under reduced pressure to produce (6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2.5]octane-6-carboxylic acid (1.06 g). MS (ESI): 256.1 (M+H+); 200.1 (M+H+-t-Bu).

Workup

  1. customat RT
  2. customThe catalyst was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-3de14147ee9c416a9ed875dbd2eb8b8c
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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