(Dimethyl sulfide)trihydroboron → HCID 71668154, compound

HRID 63317Notes

Reaction equation

HRID 63317 reaction equation
B.CSC.[CH:5]1([CH2:11][O:12][C:13]2[CH:14]=[C:15]([C:18](=[O:22])[CH2:19][C:20]#[N:21])[S:16][CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.N.CO.C(Cl)Cl>>[NH2:21][CH2:20][CH2:19][CH:18]([C:15]1[S:16][CH:17]=[C:13]([O:12][CH2:11][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:14]=1)[OH:22]

Participants

4

Reactant 3

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 21584172Ammonia methanol dichloromethaneHCID 86694608HCID 86694608, compound

Product 1

HCID 71668154HCID 71668154, compound

Procedure

Borane-dimethylsulfide reduction of 3-(4-(cyclohexylmethoxy)thiophen-2-yl)-3-oxopropanenitrile following the method used in Example 2 gave after flash chromatography purification (2%-20% 7N NH3/MeOH—CH2Cl2 gradient) Example 18 as a colorless oil. Yield (0.037 g, 43%); 1H NMR (400 MHz, CD3OD) δ 6.62 (dm J=1 Hz, 1H), 6.22 (d, J=1.4 Hz, 1H), 4.85 (m, 1H), 3.71 (d, J=6.3 Hz, 2H), 2.71-2.78 (m, 2H), 1.64-1.97 (m, 8H), 1.15-1.37 (m, 3H), 1.05-1.15 (m, 2H); RP-HPLC tR=9.63 min; ESI-MS m/z 223.1 [C13H18OS2.+H]+ or [M−H2O—CH2NH2+H]+.

Workup

  1. customgave
  2. customYield (0.037 g, 43%)

Sources & evidence

ORD record
ord-ef5f9661e04941a2be61904ef449df17
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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