Dichloromethane → HCID 71187339, compound

HRID 712794Notes

Reaction equation

[Si:1]([O:18][CH2:19][CH:20]1[CH2:26][CH:25]2[CH:23]([CH2:24]2)[CH2:22][N:21]1S(C1C=CC(C)=CC=1)(=O)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[NH4+].[Cl-].C(Cl)Cl>CO>[Si:1]([O:18][CH2:19][CH:20]1[CH2:26][CH:25]2[CH:23]([CH2:24]2)[CH2:22][NH:21]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 4-(((tert-butyldiphenylsilyl)oxy)methyl)-3-tosyl-3-azabicyclo[4.1.0]heptane (D12) (3.12 g, 6 mmol) in MeOH (430 ml), under a nitrogen atmosphere, magnesium turnings (previously flame dried) (8.46 g, 348 mmol) and NH4Cl (8.9 g, 168 mmol) were added sequentially and the mixture was stirred at 23° C. Two further additions of magnesium (4.3 g), each one after 2 hrs stirring, were done. DCM (210 ml) and NH4Cl sat. sol. (285 ml) were added to the reaction mixture. The formed emulsion was filtered through a celite pad. The organic layer was separated and washed with brine (2×55 ml). The combined organic layers were evaporated and the resulting residue was purified by SPE-SCX (20 g) cartridge. Collected ammonia fractions after solvent evaporation afforded the title compound (D13) (1.65 g).

Workup

additionwere added sequentially
filtrationThe formed emulsion was filtered through a celite pad
customThe organic layer was separated
washwashed with brine (2×55 ml)
customThe combined organic layers were evaporated
customthe resulting residue was purified by SPE-SCX (20 g) cartridge
customCollected ammonia fractions after solvent evaporation

Sources & evidence

ORD record: ord-6185e8f4d42d4a49963b1460d68032d8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181279B2

Reaction notes

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