Acetic Acid → (3-{4-[(6-Cyano-pyridin-2-ylmethyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester

HRID 1711145Notes

Reaction equation

HRID 1711145 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH:10]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH2:20][CH2:21][C:22]1[N:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 104643836-(Aminomethyl)picolinonitrileHCID 68775260[3-(4-Oxo-piperidin-1-yl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 68775165(3-{4-[(6-Cyano-pyridin-2-ylmethyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using general procedure A, [3-(4-oxo-piperidin-1-yl)-butyl]-carbamic acid tert-butyl ester (0.361 g, 1.34 mmol), 6-aminomethyl-pyridine-2-carbonitrile (0.178 g, 1.34 mmol), sodium triacetoxyborohydride (0.425 g, 2.01 mmol) and acetic acid (0.2 ml, cat.) in CH2Cl2 (15 ml) at rt for 16 h gave the crude product as a pale yellow oil. Purification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 86:12:2, v/v/v) afforded (3-{4-[(6-cyano-pyridin-2-ylmethyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.400 g, 77%) as a colorless oil. 1H NMR (CDCl3) δ 0.93 (d, 3H, J=6.0 Hz), 1.40 (s+m, 13H), 1.65 (m, 1H), 1.92 (m, 2H), 2.13 (br t, 1H, J=9.0 Hz), 2.45 (m, 2H), 2.69-2.81 (m, 3H), 3.07 (m, 1H), 3.30 (m, 1H), 3.97 (s, 2H), 5.95 (br s, 1H), 7.56 (d, 1H, J=9.0 Hz), 7.59 (d, 1H, J=9.0 Hz), 7.77 (t, 1H, J=7.5 Hz).

Workup

  1. customat rt
  2. customfor 16 h
  3. customgave the crude product as a pale yellow oil
  4. customPurification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 86:12:2, v/v/v)

Sources & evidence

ORD record
ord-af5e8c0bd7604c0b810e84771e095dde
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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