HCID 68291442, compound → HCID 68291550, compound

HRID 1408932Notes

Reaction equation

HRID 1408932 reaction equation
[OH:1][C@H:2]1[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@H:2]([OH:1])[C:3]1([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 68291442HCID 68291442, compound

Product 1

HCID 68291550HCID 68291550, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl trans-3-hydroxy-2,2-dimethylcyclopentylcarbamate (1.60 g, 6.08 mmol, isomer A from Step 1) and 10% palladium on carbon (0.323 g) in methanol (30 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 trans-3-amino-2,2-dimethylcyclopentanol (800 mg, 100% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 3.65-3.91 (1H, m), 2.95-3.17 (1H, m), 1.98-2.37 (2H, m), 1.28-1.63 (2H, m), 0.98 (3H, s), 0.84 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-bf64d90290524947b2200853bd7fba00
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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