Sodium Hydroxide → HCID 59167873, compound

HRID 1444712Notes

Reaction equation

HRID 1444712 reaction equation
FC(F)(F)C([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=O.[OH-].[Na+]>C1COCC1.CO.O>[N+:16]([C:13]1[CH:14]=[C:15]2[C:10]([CH2:9][CH2:8][CH2:7][C@H:6]2[NH2:5])=[CH:11][C:12]=1[CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58597303HCID 58597303, compound

Product 1

HCID 59167873HCID 59167873, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of (R)-2,2,2-trifluoro-N-(7-nitro-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (230 mg, 0.6 mmol) and NaOH (108 mg, 2.7 mmol) in a mixed solvent (THF/MeOH/H2O=5 mL/5 mL/1 mL) was heated at 70° C. for 3 h. After cooling to RT, the solvent was evaporated to dryness and the residue was directly loaded on column chomatography (SiO2, EtOAc to EtOAc/2M NH3 in MeOH=100:15 to 100:20) to give (R)-7-nitro-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine (200 mg) as a white solid. Similarly (R)-(1-nitro-5-(2,2,2-trifluoroacetamido)-5,6,7,8-tetrahydronaphthalen-2-yl)methyl acetate was converted to (R)-5-nitro-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine according to the above sequence of reactions.

Workup

  1. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-9798a4ed910d43deacf94040c3010e97
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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