Acetaldehyde → HCID 57659416, compound

HRID 217194Notes

Reaction equation

HRID 217194 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][CH:31]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:30][CH3:31])[CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 576595104-[(5-Furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)amino]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57659416HCID 57659416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[(5-furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)amino]-piperidine-1-carboxylic acid tert-butyl ester (Example 30, 50 mg, 120 μmol), MeCHO (6 μL, 120 μmol), and NaBH(OAc)3 (36 mg, 168 μmol) in CH2Cl2 (5 mL) was stirred for 3 d at ambient temperature. The reaction mixture was washed with water, before being dried (MgSO4) and purified by column chromatography to furnish the title compound: RT=2.40 min; m/z (ES+)=428.2 [M+H]+.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialbefore being dried (MgSO4)
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-448cf4dac29e4e039f46b9f463d4af8c
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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