Sodium borohydride → 2-(2,6-dichloro-4-fluorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine

HRID 2202680Notes

Reaction equation

HRID 2202680 reaction equation
[CH3:1][C:2]1([CH:5]=O)[CH2:4][CH2:3]1.[Cl:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([Cl:15])[C:9]=1[CH:16]([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:17][NH2:18].[BH4-].[Na+]>CO>[Cl:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([Cl:15])[C:9]=1[CH:16]([O:19][Si:20]([CH2:21][CH3:22])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:17][NH:18][CH2:5][C:2]1([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 101976191-Methylcyclopropane-1-carbaldehydeHCID 1235262232-(2,6-Dichloro-4-fluorophenyl)-2-((triethylsilyl)oxy)ethanamine

Product 1

HCID 1239140462-(2,6-dichloro-4-fluorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamineYield 72.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-methylcyclopropanecarbaldehyde (31.6 mg, 0.375 mmol) and 2-(2,6-dichloro-4-fluorophenyl)-2-((triethylsilyl)oxy)ethanamine (127 mg, 0.375 mmol) in MeOH (1.9 ml) was stirred at room temperature for 3 h. NaBH4 (14.20 mg, 0.375 mmol) was added in portions and the mixture was stirred at room temperature for 40 min. The mixture was concentrated and purified by prep TLC eluted with 5% MeOH/DCM to provide 2-(2,6-dichloro-4-fluorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine (111 mg, 0.273 mmol, 72.8% yield). 1H NMR (500 MHz, CDCl3) δ 7.29 (s, 1H), 7.06-7.10 (m, 2H), 5.56 (br. s., 1H), 3.33 (t, J=10.51 Hz, 1H), 2.81 (d, J=9.17 Hz, 1H), 2.60-2.67 (m, 1H), 2.44 (d, J=11.86 Hz, 1H), 1.46-1.59 (m, 1H), 1.13 (s, 3H), 0.85-0.96 (m, 9H), 0.50-0.63 (m, 6H), 0.36 (br. s., 2H), 0.30 (br. s., 2H); LCMS (ESI) m/z 406.0 (M+H)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 min
  2. concentrationThe mixture was concentrated
  3. custompurified by prep TLC
  4. washeluted with 5% MeOH/DCM

Sources & evidence

ORD record
ord-c52089ec5c734e0dbb509045e17885f2
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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