Ethanol → HCID 178452487, compound
Reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[C:14](=O)[CH2:13][C@@H:12]([CH:16]2[CH2:18][CH2:17]2)[N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCO.O.[NH2:30]N.CCOC(C)=O.C[N:39]([CH:41](OC)OC)C>>[Si:1]([O:8][CH2:9][CH:10]1[C:14]2=[N:30][NH:39][CH:41]=[C:13]2[C@@H:12]([CH:16]2[CH2:17][CH2:18]2)[N:11]1[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 110 °C
Procedure
(5S)-tert-Butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-cyclopropyl-3-oxopyrrolidine-1-carboxylate (34) (1.52 g, 4.11 mmol) was dissolved in DMF-DMA (5 mL) and heated to 110° C. for 1 h. The reaction mixture was concentrated under vacuum and to the resulting residue was added EtOH (8 mL) and hydrazine monohydrate (0.99 mL, 20.5 mmol). The resulting solution was stirred at rt for 5 h after which EtOAc (10 mL) was added. The solution was washed with brine (10 mL), dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1) to give 1.41 g (87%) of (4R)-tert-butyl 6-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate (35). Retention time (min)=2.086, method [1], MS (m/z) 394.2 (M+H)+.
Workup
- concentrationThe reaction mixture was concentrated under vacuum and to the resulting residue
- additionwas added
- washThe solution was washed with brine (10 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
- custompurified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1)
Sources & evidence
- ORD record
- ord-897859494ff14ec5b573cecdf295637c
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977368B2
Reaction notes
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