Sodium Hydroxide → HCID 67773433, compound
Reaction equation
[N:1]1([C:5](=O)[C@@H:6]([NH:10][C:11](=O)OC(C)(C)C)[CH:7]2[CH2:9][CH2:8]2)[CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>C1COCC1.CCO>[N:1]1([CH2:5][C@H:6]([CH:7]2[CH2:9][CH2:8]2)[NH:10][CH3:11])[CH2:4][CH2:3][CH2:2]1Participants
Conditions
- Temperature
- 60 °C
Procedure
To a solution of (S)-tert-butyl 2-(azetidin-1-yl)-1-cyclopropyl-2-oxoethylcarbamate (Compound B1) (1.4 g, 5.50 mmol) in THF (40 mL) was a 1M solution of LAH in THF (16 mL, 16.0 mmol) dropwise added (over approximately 10 min) at −20° C. under a nitrogen atmosphere. The resultant mixture was stirred at rt for 1 h and heated at 60° C. over night. The reaction was cooled to −5° C. and Na2SO4×10H2O (ca 5 g) and NaOH (2M, 2 mL) was added. The mixture was diluted with EtOH (100 mL) and the resultant mixture was warmed to rt and stirred for 1 h. The mixture was filtered and the solid was washed with THF. The filtrate was concentrated under reduced pressure to give the title compound (0.31 g, 37%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 0.03, 0.26, 0.33-0.46, 0.50-0.64, 1.51, 2.00-2.12, 2.42-2.48, 2.49, 2.56, 3.19. Total no of protons: 17. LCMS (M+H)+: 155.
Workup
- additiondropwise added (over approximately 10 min) at −20° C. under a nitrogen atmosphere
- temperatureThe reaction was cooled to −5° C.
- filtrationThe mixture was filtered
- washthe solid was washed with THF
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-507e0bc67d46420bb56e2f210af34d1b
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361998B2
Reaction notes
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