Methylamine → HCID 57514177, compound

HRID 73262Notes

Reaction equation

HRID 73262 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH:9]=O)[CH:5]=[CH:6][CH:7]=1.[CH3:20][NH2:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O.CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH2:9][NH:21][CH3:20])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57514175HCID 57514175, compound

Product 1

HCID 57514177HCID 57514177, compoundYield 60.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of tert-butyl 2-(3-bromophenyl)-1-oxopropan-2-ylcarbamate (CD2; R4=Me) (1.0 g, 3 mmol) in dichloroethane (50 mL) was added methylamine (0.48 g, 6.1 mmol, 2 eq) in water (40%) and 1 mL of AcOH. The solution was allowed to stir at RT for 1 h followed by the addition of sodium triacetoxyborohydride (1.8 g, 8.5 mmol, 2.8 eq). The resulting mixture was stirred at RT for 16 h and quenched with MeOH. After stirring for 30 min the mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel by eluting with EtOAc/MeOH to give 0.62 g (60%) of tert-butyl 2-(3-bromophenyl)-1-(methylamino)propan-2-ylcarbamate (CD3; R1=Me, R4=Me) as a colorless oil. 1H NMR (CDCl3) δ 7.47 (bs, 1H), 7.37 (m, 1H), 7.27 (m, 1H), 7.23 (m, 1H), 5.97 (bs, 1H), 3.18-2.82 (m, 2H), 2.45 (s, 3H), 1.74 (s, 3H), 1.40 (s, 9H). MS (ESI) m/e 342.9 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at RT for 16 h
  2. customquenched with MeOH
  3. stirringAfter stirring for 30 min the mixture
  4. concentrationwas concentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel
  6. washby eluting with EtOAc/MeOH

Sources & evidence

ORD record
ord-cd4dc1cc9d9145cc9c940c1d535925e4
Source dataset
uspto-grants-2014_09
Patent number
US08829036B2

Reaction notes

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