Acetic Acid → 3-Cyclohexyl-3-hydroxy-1-(tert-butoxycarbonyl)azetidine

HRID 540372Notes

Reaction equation

HRID 540372 reaction equation
C(O)(=O)C.[OH:5][C:6]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1.[H][H]>CO.[Rh]>[CH:17]1([C:6]2([OH:5])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:7]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 65810524Tert-butyl 3-hydroxy-3-phenylazetidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 659194093-Cyclohexyl-3-hydroxy-1-(tert-butoxycarbonyl)azetidineYield 100%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

0.5 ml of acetic acid and 40 mg of rhodium on alumina 5% are added to a solution containing 117 mg (0.470 mmol) of 3-hydroxy-3-phenyl-1-(tert-butoxy-carbonyl)azetidine (cf. procedure 1-2-1) dissolved in 4 ml of methanol. The reaction medium is placed at 4 bar of hydrogen and heated at 85° C. for 4 hours. The catalyst is filtered off and washed with methanol and the solvents are evaporated off. 120 mg in the form of a beige powder are obtained with a yield of 100%.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol
  3. customthe solvents are evaporated off
  4. custom120 mg in the form of a beige powder are obtained with a yield of 100%

Sources & evidence

ORD record
ord-14da5c11b6ba457f927e65702334bbce
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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