[(S)-3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-carbamic acid benzyl ester → (S)-6-((S)-3-amino-4-hydroxy-butyl)-6-aza-spiro[2.5]octan-4-ol

HRID 1261837Notes

Reaction equation

HRID 1261837 reaction equation
C(OC(=O)[NH:10][C@H:11]([CH2:23][OH:24])[CH2:12][CH2:13][N:14]1[CH2:21][CH2:20][C:17]2([CH2:19][CH2:18]2)[C@H:16]([OH:22])[CH2:15]1)C1C=CC=CC=1>CO.[Pd]>[NH2:10][C@H:11]([CH2:23][OH:24])[CH2:12][CH2:13][N:14]1[CH2:21][CH2:20][C:17]2([CH2:19][CH2:18]2)[C@H:16]([OH:22])[CH2:15]1

Participants

4

Reactant 1

HCID 67079922[(S)-3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-carbamic acid benzyl ester

Product 1

HCID 67080071(S)-6-((S)-3-amino-4-hydroxy-butyl)-6-aza-spiro[2.5]octan-4-olYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [(S)-3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-carbamic acid benzyl ester (350 mg, 1.00 mmol) in MeOH (5 mL) was stirred for 1½ h at room temperature under a hydrogen atmosphere (1 bar) in the presence of palladium (10% on activated charcoal, 35 mg), then insoluble material was removed by filtration through diatomaceous earth. The filtrate was evaporated to afford the title compound (215 mg, 100%) Colourless gum, MS (ISP)=215.3 (M+H)+.

Workup

  1. custominsoluble material was removed by filtration through diatomaceous earth
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-3d7f903a3c1f445bac0c7be0d5c92686
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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