4-(N-Boc-amino)piperidine → HCID 86635316, compound

HRID 656915Notes

Reaction equation

HRID 656915 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[O:12][CH2:13][CH2:14][O:15][C:5]=3[C:4]=2[N:3]1[CH2:16][CH:17]=O.[NH:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21][CH2:20]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl.CO>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[O:12][CH2:13][CH2:14][O:15][C:5]=3[C:4]=2[N:3]1[CH2:16][CH2:17][N:19]1[CH2:20][CH2:21][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86635317HCID 86635317, compound

Product 1

HCID 86635316HCID 86635316, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

(9-oxo-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10(9H)-yl)acetaldehyde (1.5 g; 6.12 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (1.84 g; 9.18 mmol) were dissolved in a 1:1 mixture of chloroform and MeOH (50 ml:50 ml) and stirred at rt for 30 mins. NaBH(OAc)3 (5.81 g; 27.54 mmol) was added and the reaction left overnight. The solvents were then removed and the residues purified by column chromatography on silica gel using a 0-12% MeOH/DCM gradient to give the desired product (1 g; 38%).

Workup

  1. waitthe reaction left overnight
  2. customThe solvents were then removed
  3. customthe residues purified by column chromatography on silica gel using a 0-12% MeOH/DCM gradient

Sources & evidence

ORD record
ord-9f765ff16fc54f7d97422557706eda9e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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