Tert-butyl 3-hydroxyazetidine-1-carboxylate → HCID 178452414, compound

HRID 717261Notes

Reaction equation

HRID 717261 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.CC(C)([O-])C.[Na+].[C:19]([C:23]1[O:27]/[C:26](=[N:28]\[C:29](=[O:41])[C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:31]=2F)/[N:25]([CH2:42][C@H:43]2[CH2:47][CH2:46][CH2:45][O:44]2)[CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>C1COCC1.O>[C:19]([C:23]1[O:27]/[C:26](=[N:28]\[C:29]([C:30]2[CH:35]=[C:34]([C:36]([F:38])([F:37])[F:39])[CH:33]=[CH:32][C:31]=2[O:1][CH:2]2[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]2)=[O:41])/[N:25]([CH2:42][C@H:43]2[CH2:47][CH2:46][CH2:45][O:44]2)[CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 23676156Sodium t-butoxideHCID 178441318HCID 178441318, compound

Product 1

HCID 178452414HCID 178452414, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (167 mg, 0.965 mmol) in THF (2 mL) was added sodium tert-butoxide (93 mg, 0.965 mmol). The reaction was stirred at room temperature for 20 min. The reaction was cooled to 0° C. and a solution of Example 95A (200 mg, 0.483 mmol) in THF (1 mL) was added. The reaction was stirred at 0-5° C. for 2 h. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The organic layer was combined and dried over MgSO4, filtered and concentrated to afford the title compound 260 mg (93%). MS (DCI/NH3) m/z 568 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringThe reaction was stirred at 0-5° C. for 2 h
  3. extractionextracted with EtOAc (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ca6faea232f4976851664906b9abf72
Source dataset
uspto-grants-2015_11
Patent number
US09193713B2

Reaction notes

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