benzyl (3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-4,5-dimethylpiperidine-1-carboxylate → tert-Butyl [(3R,4S,5S)-4-hydroxy-4,5-dimethylpiperidin-3-yl]carbamate

HRID 1499628Notes

Reaction equation

HRID 1499628 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@:14]([OH:16])([CH3:15])[C@@H:13]([CH3:17])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[OH:16][C@@:14]1([CH3:15])[C@@H:13]([CH3:17])[CH2:12][NH:11][CH2:10][C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86726847benzyl (3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-4,5-dimethylpiperidine-1-carboxylate

Product 1

HCID 86726846tert-Butyl [(3R,4S,5S)-4-hydroxy-4,5-dimethylpiperidin-3-yl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of benzyl (3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-4,5-dimethylpiperidine-1-carboxylate (100 mg, 0.265 mmol) in MeOH (5.0 mL), 10 wt % Pd on carbon (33 mg) was added. The reaction mixture was stirred at room temperature under a hydrogen atmosphere (balloon pressure) for 3 h. The reaction was filtered through a pad of diatomaceous earth (eluted with MeOH), and then concentrated under reduced pressure. The resulting crude product was used directly in the next step without further purification (60 mg, 92%). LCMS calc. for C12H25N2O3 (M+H)+: m/z=245.2. found 245.0.

Workup

  1. filtrationThe reaction was filtered through a pad of diatomaceous earth (eluted with MeOH)
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting crude product was used directly in the next step without further purification (60 mg, 92%)

Sources & evidence

ORD record
ord-8106f06e3ecf48e98031dd9559cb2876
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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