Methanol → trans-(1,1-Diethyl-7-hydroxy-3-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:18]2[CH:9]1[C:10]([CH2:22][CH3:23])([CH2:20][CH3:21])[C:11]1[C:16]([CH2:17]2)=[CH:15][CH:14]=[C:13]([OH:19])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:41][OH:42]>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[C@H:18]([O:42][CH3:41])[CH2:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=2)[C:10]1([CH2:20][CH3:21])[CH2:22][CH3:23])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 3
Product 1
Conditions
- Temperature
- 40 °C
Procedure
To a slurry of 7,7-diethyl-5-hydroxy-1a,2,7,7a-tetrahydro-1-aza-cyclopropa[b]naphthalene-1-carboxylic acid tert-butyl ester (170.0 g, 535.6 mmol) and methanol (1700 mL) was added pyridinium p-toluenesulfonate (13.4 g, 53.6 mmol) and the reaction mixture was stirred at 40° C. for 4 h. The volume was reduced by rotary evaporation to ˜300 mL resulting in a thick white slurry. The product was isolated by filtration; the filter cake was washed with cold methanol (50 mL) and dried in air for 3 h to yield the title compound (150 g). The filtrate was reduced to ˜50 mL and stirred at 0° C. for 2 h, filtered, and dried to yield additional product (25 g).
Workup
- customThe volume was reduced by rotary evaporation to ˜300 mL
- customresulting in a thick white slurry
- customThe product was isolated by filtration
- washthe filter cake was washed with cold methanol (50 mL)
- customdried in air for 3 h
Sources & evidence
- ORD record
- ord-a218af753c464f52a154b976d8eec2a4
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703791B2
Reaction notes
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