1,4-Dioxane hydrochloride → (1S,3R)-3-((benzyloxy)carbonyl)-2,2-dimethylcyclobutane-1-carboxylic acid

HRID 2179742Notes

Reaction equation

HRID 2179742 reaction equation
[CH3:1][C:2]1([CH3:23])[C@@H:5]([C:6]([O:8]C(C)(C)C)=[O:7])[CH2:4][C@H:3]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].Cl.O1CCOCC1>C(OCC)(=O)C>[CH2:16]([O:15][C:13]([C@@H:3]1[CH2:4][C@H:5]([C:6]([OH:8])=[O:7])[C:2]1([CH3:23])[CH3:1])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66859968(1R,3S)-1-benzyl 3-tert-butyl 2,2-dimethylcyclobutane-1,3-dicarboxylate

Product 1

HCID 15819066(1S,3R)-3-((benzyloxy)carbonyl)-2,2-dimethylcyclobutane-1-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,3S)-1-benzyl 3-tert-butyl 2,2-dimethylcyclobutane-1,3-dicarboxylate (step 3, 1.0 g) dioxane-HCl (10 ml) was added at about 0° C. under nitrogen atmosphere. The reaction mixture was stirred for about 12 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give crude product, which upon column chromatography to afford the title compound (800 mg, 97.2% Yield). 1H NMR (300 MHz, CDCl3): δ 7.35 (5H, s), 5.12 (2H, d, J=2.7 Hz), 2.84 (2H, m), 2.63 (1H, m), 2.0 (1H, m), 1.35 (3H, s), 0.99 (3H, s); Mass: [M+H]+ 263.1 (20%), 285.1 [M+Na]+.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. washwashed with water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give crude product, which upon column chromatography

Sources & evidence

ORD record
ord-9ad64c7ab31e4aea8b308e2806ff2dfa
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…