HCID 68291601, compound → HCID 68291783, compound

HRID 1408930Notes

Reaction equation

HRID 1408930 reaction equation
[OH:1][C@:2]1([CH3:20])[CH2:6][CH2:5][C@@H:4]([NH:7]C(=O)OCC2C=CC=CC=2)[C:3]1([CH3:19])[CH3:18]>[Pd].CO>[NH2:7][C@@H:4]1[CH2:5][CH2:6][C@@:2]([CH3:20])([OH:1])[C:3]1([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 68291601HCID 68291601, compound

Product 1

HCID 68291783HCID 68291783, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl (1R,3R)-3-hydroxy-2,2,3-trimethylcyclopentylcarbamate (900 mg, 3.24 mmol, from Step 1) and 10% palladium on carbon (173 mg) in methanol (15 mL) was stirred under hydrogen at 20 psi for 2 h. The mixture was filtered to remove the catalyst. The filtrate was concentrated to give (1R,3R)-3-amino-1,2,2-trimethylcyclopentanol (450 mg, 97% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 3.11-3.52 (1 H, m), 1.98-2.43 (1 H, m), 1.75-1.93 (1 H, m), 1.56-1.71 (1 H, m), 1.27-1.48 (1 H, m), 1.16 (3 H, s), 0.93 (3 H, s), 0.72 (3 H, s).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a90a9b0ea48a4099af5814a21e195ed6
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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