Dimethyl Sulfide → HCID 59627237, compound

HRID 1523235Notes

Reaction equation

HRID 1523235 reaction equation
[NH2:1][C@:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)=O.S(C)C>C1COCC1>[C:15]1([C@@:2]([NH2:1])([CH3:14])[CH2:3][CH2:4][NH:6][C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 59627240HCID 59627240, compound

Product 1

HCID 59627237HCID 59627237, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (R)-3-amino-3-phenyl-N-m-tolylbutanamide (218 mg, 0.81 mmol) in THF (5 mL) was cooled to 0° C. under N2 and 2M BH3.Me2S (1 mL, 2 mmol) was added. Then the mixture was stirred at 80° C. overnight. The reaction mixture was quenched with MeOH and concentrated. The residue was purified by preparative TLC to afford (R)-3-phenyl-N1-m-tolylbutane-1,3-diamine (50 mg, 24%). 1H NMR (CDCl3): 1.59-1.62 (m, 7H), 1.30-1.35 (m, 4H), 2.15-2.20 (m, 3H), 2.40-2.65 (m, 2H), 2.98-3.05 (m, 2H), 3.35-3.45 (m, 1H), 3.60-3.65 (m, 6H), 3.75-3.80 (m, 1H), 6.40-6.60 (m, 2H), 6.90-7.01 (m, 1H), 7.25-7.40 (m, 4H), 7.45-7.52 (m, 2H).

Workup

  1. customThe reaction mixture was quenched with MeOH
  2. concentrationconcentrated
  3. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-8626d72f2c934d2abd05e77668fcd57b
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

Loading…