6-(tert-butoxycarbonyl)-6-azaspiro[2.5]octane-5(S)-carboxylic acid benzyl ester → (S)-6-(tert-Butoxycarbonyl)-6-azaspiro[2.5]octane-5-carboxylic acid

HRID 536583Notes

Reaction equation

HRID 536583 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10][C@H:9]1[C:16]([O:18]CC1C=CC=CC=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:12][CH2:13]2)[CH2:10][C@H:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 668483686-(tert-butoxycarbonyl)-6-azaspiro[2.5]octane-5(S)-carboxylic acid benzyl ester2×

Product 1

HCID 66848235(S)-6-(tert-Butoxycarbonyl)-6-azaspiro[2.5]octane-5-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 5-benzyl ester 6-tert-butyl ester (intermediate 16, 110 g, 0.32 mol, ee:66%) in anhydrous methanol (1 L) was added Pd/BaSO4 (50 g) under hydrogen, the reaction mixture was stirred at room temperature for overnight. The resulting mixture was filtered and the liquid phase was evaporated to give 68 g of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 6-tert-butyl ester (light white solid, yield:85%) which was recrystallized with PE/EtOAc (4:1) to give 38 g of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 6-tert-butyl ester.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe liquid phase was evaporated

Sources & evidence

ORD record
ord-9dee9b7796434ede9d11b4c0812155b1
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Reaction notes

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