(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate → (1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acid

HRID 2179728Notes

Reaction equation

HRID 2179728 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([O:11]CC2C=CC=CC=2)=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([OH:11])=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86650107(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate

Product 1

HCID 11183048(1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acidYield 54.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of (1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate (0.650 g, 2.36 mmol) in EtOAc (10 ml) at room temperature, 10% Pd/C (catalytic amount) were added and the reaction mixture was stirred under H2 gas atmosphere at room temperature for about 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through celite bed. The obtained filtrate was concentrated under reduced pressure to afford title compound as an off white solid. Wt: 0.240 g; Yield: 54.9%; 1H NMR (300 MHZ, CD3OD): δ 8.09 (d, J=3.0 Hz, 1H), 4.08-3.96 (m, 1H), 2.62-2.58 (m, 1H), 2.20-2.15 (m, 2H), 1.93 (s, 3H), 1.26 (s, 3H), 0.92 (s, 3H); Mass: [M+1]+ 186 (70%), [M+Na]+ 208 (93%). IR (KBr, cm−1): 3349, 2962, 1697, 1624, 1557, 1428, 1377, 1257, 1075, 988, 920, 736; M.R: 194.7° C.-216.2° C.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. filtrationthe reaction mixture was filtered through celite bed
  3. concentrationThe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-36ff39b084814270ae1bb442be98ed00
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…