HCID 86707712, compound → HCID 86707713, compound

HRID 1408965Notes

Reaction equation

HRID 1408965 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:16][CH2:15][C@:14]([CH3:21])([C:17]([O:19][CH3:20])=[O:18])[C:13]1([CH3:23])[CH3:22])=O)C1C=CC=CC=1>[Pd].C(O)C>[NH2:11][C@@H:12]1[CH2:16][CH2:15][C@:14]([CH3:21])([C:17]([O:19][CH3:20])=[O:18])[C:13]1([CH3:23])[CH3:22]

Participants

4

Reactant 1

HCID 86707712HCID 86707712, compound

Product 1

HCID 86707713HCID 86707713, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a flask, charged with 10% palladium on carbon (90 mg, 0.845 mmol), under a steady nitrogen flow was added ethanol (5 ml), followed by addition of a solution of (1S,3R)-methyl 3-(benzyloxycarbonylamino)-1,2,2-trimethylcyclopentanecarboxylate (900 mg, 2.82 mmol) in ethanol (11.300 ml). The flask was evacuated and flushed with hydrogen and then filled with one atmosphere of hydrogen. The reaction was stirred at room temperature for 14 hrs. The flask was evacuated and backfilled with nitrogen. The suspension was filtered through a pad of Celite. The Celite cake was washed with ethanol (3×, 20 ml). The ethanol wash was concentrated under reduced pressure to yield the title compound (478 mg, 2.58 mmol, 92% yield) as a colorless oil. LC/MS found [M+H]+=186.3. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.68 (s, 3H), 3.10 (t, J=9.1 Hz, 1H), 2.57-2.47 (m, 1H), 2.11-2.02 (m, 1H), 1.46-1.35 (m, 2H), 1.19-1.17 (m, 3H), 1.07-1.03 (m, 3H), 0.72 (s, 3H).

Workup

  1. customThe flask was evacuated
  2. customflushed with hydrogen
  3. additionfilled with one atmosphere of hydrogen
  4. customThe flask was evacuated
  5. filtrationThe suspension was filtered through a pad of Celite
  6. washThe Celite cake was washed with ethanol (3×, 20 ml)
  7. washThe ethanol wash
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-54ecdfa5a8b940d5b7acfdaaa7c674f2
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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