(S)-6-benzyl-6-aza-spiro[2,5]octan-4-ol → (4S)-6-Azaspiro[2.5]octan-4-ol

HRID 655497Notes

Reaction equation

HRID 655497 reaction equation
C([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[C@H:10]([OH:16])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH2:12]1[C:11]2([CH2:14][CH2:15][NH:8][CH2:9][C@H:10]2[OH:16])[CH2:13]1

Participants

4

Reactant 1

HCID 25204267(S)-6-benzyl-6-aza-spiro[2,5]octan-4-ol

Product 1

HCID 44541813(4S)-6-Azaspiro[2.5]octan-4-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

100 mg (S)-6-benzyl-6-aza-spiro[2.5]octan-4-ol were dissolved in 1 ml methanol and hydrogenated over palladium on barium sulfate. After de-benzylation (IPC by GC), the catalyst was filtered and the filtrate was concentrated under reduced pressure to provide the title compound. The amino alcohol was treated with di-tert-butyl-dicarbonate in methanol in the presence of triethylamine. The crude tert-butoxycarbonyl-protected amine product was analyzed by chiral GC (BGB-176; 30 m×0.25 mm; 80° C. to 210° C. in 43 min) and proved to be identical with intermediate 2b.

Workup

  1. filtrationAfter de-benzylation (IPC by GC), the catalyst was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc684744d4034f1f8632f517bbd0a673
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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