Methanol → HCID 81689841, compound

HRID 2277041Notes

Reaction equation

HRID 2277041 reaction equation
[OH:1][C@@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:7]=1)[CH2:3][C:4]#[N:5].CO>C1COCC1>[NH2:5][CH2:4][CH2:3][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:7]=1)[OH:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 90406331HCID 90406331, compound

Product 1

HCID 81689841HCID 81689841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

BH3-DMS (0.56 g, 7.4 mmol) was added dropwise to a solution of hydroxynitrile (14) (0.65 g, 2.4 mmol) in dry THF (50 mL). The reaction mixture was refluxed 18 h at 65° C. After completion of the reaction (as monitored by TLC) the MeOH (15 mL) was added to the reaction mixture which was stirred at rt for an additional 1 h. The mixture was then concentrated under reduced pressure followed by purification by column chromatography (100-200 silica mesh, 4-6% MeOH in DCM) to give Example 1 as a white solid. Yield (0.75 g, 99%); 1H NMR (400 MHz, DMSO-d6) δ 7.80 (bs, 3H), 7.24 (t, J=8.0 Hz, 1H), 6.89-6.87 (m, 2H), 6.82-6.80 (m, 1H), 5.54 (bs, 1H), 4.65 (bs, 1H), 3.87 (dd, J=11.4, 2.8 Hz, 2H), 3.81 (d, J=6.4 Hz, 2H), 3.37-3.30 (m, 2H), 2.87-2.79 (m, 2H), 2.02-1.96 (m, 1H), 1.88-1.80 (m, 2H), 1.69-1.65 (m, 2H), 1.34-1.27 (m, 2H); RP HPLC tR=1.10 min, 94.5% (AUC); ESI MS m/z 266.27 [M+H]+.

Workup

  1. additionwas added to the reaction mixture which
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customfollowed by purification by column chromatography (100-200 silica mesh, 4-6% MeOH in DCM)

Sources & evidence

ORD record
ord-0e73614c1e7d4c95abbf9a3af9c0dbe7
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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