HCID 67286081, compound → HCID 67290743, compound

HRID 2191382Notes

Reaction equation

HRID 2191382 reaction equation
[NH2:1][CH2:2][C@H:3]([C@H:5]1[C@H:12]2[C@H:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[CH:7]=[CH:6]1)[OH:4]>CO.[Pd]>[NH2:1][CH2:2][C@H:3]([C@H:5]1[C@H:12]2[C@H:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[CH2:7][CH2:6]1)[OH:4]

Participants

4

Reactant 1

HCID 67286081HCID 67286081, compound

Product 1

HCID 67290743HCID 67290743, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-2-amino-1-((3aS,4S,6aR)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (2-5) (3.22 g, 16.2 mmol, 1.0 equiv) was dissolved in MeOH (150 mL) and 10% Pd/C (1.72 g, 16.2 mmol, 1.0 equiv) was carefully added. The resulting mixture stirred for 2 hours under a H2 atmosphere. The reaction mixture was filtered through a plug of celite, and the solids were washed with MeOH (4×50 mL). The filtrate was concentrated to afford desired (S)-2-amino-1-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (2-6) as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 4.65 (s, 1H); 4.35 (s, 1H); 3.67 (s, 2H); 3.50 (s, 1H); 3.04 (t, J=7.3 Hz, 1H); 2.91 (d, J=27.3 Hz, 1H); 2.70 (d, J=11.1 Hz, 1H); 2.26-2.21 (m, 1H); 1.96 (d, J=14.6 Hz, 2H); 1.89 (d, J=20.3 Hz, 1H); 1.77 (s, 1H); 1.52-1.41 (m, 3H); 1.35-1.26 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washthe solids were washed with MeOH (4×50 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-937f374a7bb34096b97257cb5556c153
Source dataset
uspto-grants-2012_12
Patent number
US08329697B2

Reaction notes

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