(Dimethyl sulfide)trihydroboron → HCID 86694656, compound

HRID 63345Notes

Reaction equation

HRID 63345 reaction equation
B.CSC.[C:5]([CH2:7][C@H:8]([C:10]1[N:15]=[C:14]([O:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[CH:13]=[CH:12][CH:11]=1)[OH:9])#[N:6].N.CO.C(Cl)Cl>>[NH2:6][CH2:5][CH2:7][C@H:8]([C:10]1[N:15]=[C:14]([O:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])[CH2:22][CH2:23]2)[CH:13]=[CH:12][CH:11]=1)[OH:9]

Participants

4

Reactant 3

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 21584172Ammonia methanol dichloromethaneHCID 86694657(R)-benzyl 4-(((6-(2-cyano-1-hydroxyethyl)pyridin-2-yl)oxy)methyl)piperidine-1-carboxylate

Product 1

HCID 86694656HCID 86694656, compound

Procedure

Borane-dimethylsulfide reduction of (R)-benzyl 4-(((6-(2-cyano-1-hydroxyethyl)pyridin-2-yl)oxy)methyl)piperidine-1-carboxylate following the method described in Example 2 gave after flash chromatography purification (30%-40% 7N NH3/MeOH—CH2Cl2 gradient) Example 36 as a colorless oil. Yield (0.27 g, 27%); 1H NMR (400 MHz, CD3OD) δ 7.63 (t, J=8.4 Hz, 1H), 7.38-7.25 (m, 5H), 7.03 (d, J=7.2 Hz, 1H), 6.62 (d, J=8.0 Hz, 1H), 5.10 (s, 2H), 4.70-4.62 (m, 1H), 4.21-4.10 (m, 4H), 2.88-2.78 (m, 4H), 2.02-1.70 (m, 5H), 1.34-1.20 (m, 2H); RP-HPLC tR=9.40 min; ESI-MS m/z 400.3 [M+H]+.

Workup

  1. customgave
  2. customYield (0.27 g, 27%)

Sources & evidence

ORD record
ord-b0ed251b416b42a1ba8d0e813a587506
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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