Acetic Acid → HCID 67272553, compound

HRID 1624234Notes

Reaction equation

HRID 1624234 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:15]1[C:24]2[CH:23]([NH2:25])[CH2:22][CH2:21][CH2:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:25][CH:23]2[C:24]3[N:15]=[CH:16][CH:17]=[CH:18][C:19]=3[CH2:20][CH2:21][CH2:22]2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 113555648-Amino-5,6,7,8-tetrahydroquinoline

Product 1

HCID 67272553HCID 67272553, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using general procedure B: Reaction of Boc-4-piperidone (641 mg, 3.22 mmol 5,6,7,8-Tetrahydro-quinolin-8-ylamine (476 mg, 3.22 mmol), sodium triacetoxyborohydride (1.36 g, 6.44 mmol) and acetic acid (0.25 mL) in THF (25 mL) at room temperature under N2 for 20 min afforded the title compound (1.05 g, 98%) as a yellow oil.

Sources & evidence

ORD record
ord-b11e58c954164c23967514cdebf6cc48
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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