Benzenemethanamine, 3-chloro- → HCID 68774079, compound

HRID 1711165Notes

Reaction equation

HRID 1711165 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH2:25].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C(O)(=O)C>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[C:21]([Cl:20])[CH:22]=2)[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 77802Benzenemethanamine, 3-chloro-HCID 5049666Sodium triacetoxyborohydrideHCID 59458203HCID 59458203, compound

Product 1

HCID 68774079HCID 68774079, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Following general procedure A: to a solution of [(R)-3-(4-oxo-piperidin-1-yl)-butyl]-carbamic acid tert-butyl ester (0.25 g, 0.94 mmol) in CH2Cl2 (20 ml) was added 3-chloro-benzylamine (0.14 ml, 1.13 mmol) and the mixture was stirred for 5 min. NaBH(OAc)3 (0.30 g, 1.41 mmol) and acetic acid (10 drops) were added and the mixture was stirred at rt under N2 overnight. The crude product was purified by flash chromatography (CH2Cl2, 5% MeOH, 1% NH4OH) to afford {(R)-3-[4-(3-chloro-benzylamino)-piperidin-1-yl]-butyl}-carbamic acid tert-butyl ester as a yellow oil (305 mg, 82%). 1H NMR (CDCl3) δ 0.92-0.94 (d, 3H, J=6 Hz), 1.27-1.39 (m, 2H), 1.44 (s, 9H), 1.60-1.72 (m, 2H), 1.82-1.97 (m, 2H), 2.02-2.14 (m, 1H), 2.32-2.51 (m, 2H), 2.68-2.87 (m, 3H), 3.05-3.11 (m, 1H), 3.23-3.37 (m, 1H), 3.79 (s, 2H), 4.40 (s, 1H), 6.01 (br s, 1H), 7.16-7.25 (m, 3H), 7.33 (s, 1H).

Workup

  1. stirringthe mixture was stirred at rt under N2 overnight
  2. customThe crude product was purified by flash chromatography (CH2Cl2, 5% MeOH, 1% NH4OH)

Sources & evidence

ORD record
ord-62bdb0d77c824f70b06b37a1164b84fb
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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