Stannous chloride dihydrate → Methyl cis(+/-)-2-amino-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]([N+:28]([O-])=O)=[C:22]([CH:27]=2)[C:23]([O:25][CH3:26])=[O:24])[CH2:14][C@H:13]1[O:31][CH3:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C.C1COCC1>[NH2:28][C:21]1[CH:20]=[CH:19][C:18]([N:15]2[CH2:16][CH2:17][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[C@H:13]([O:31][CH3:32])[CH2:14]2)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
Methyl cis(±)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-nitrobenzoate obtained in Example (185a) was dissolved in ethanol (20 ml) and THF (20 ml). Tin (II) chloride dihydrate (4.4 g, 19.6 mmol) was added, and the mixture was stirred at 75° C. overnight. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with aqueous sodium bicarbonate and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, 900 mg of the title compound was obtained as an oily substance.
Workup
- concentrationThe reaction solution was concentrated under reduced pressure
- additiondiluted with ethyl acetate
- washwashed with aqueous sodium bicarbonate and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentration under reduced pressure
Sources & evidence
- ORD record
- ord-6b102dd6d17a4d5abbb6cc0bb1f9f2a4
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536197B2
Reaction notes
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