Dichloromethane → HCID 56654760, compound

HRID 1749159Notes

Reaction equation

HRID 1749159 reaction equation
[C:1]1([C:7]2([CH2:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[O:13])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].ClCCl>ClCCl.CO>[C:1]1([C:7]2([CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[OH:13])[CH2:10][CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 66750139HCID 66750139, compound

Product 1

HCID 56654760HCID 56654760, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of Example 68E (1.5 g) in 27 mL of dichloromethane:methanol (9:1) was added NaBH4 (0.1 g, 2.6 mmol). The reaction was monitored by LC/MS, dichloromethane was added to the solution upon completion of the reaction. The mixture was washed with water, dried over Na2SO4, and filtered. The crude product was purified by preparative-HPLC (eluted with petroleum ether/EtOAc=5:1) to afford title compound (0.4 g, 1.6 mmol, 37.2%). LC-Ms: ESI-MS (M+H+): m/e=254.2. 1H NMR (400 MHz, CDCl3), 6 (ppm): 10.82 (br, 2H), 8.59 (d, J=5.2 Hz, 1H), 8.06 (td, J=2.0 Hz, J2=7.8 Hz, 1H), 7.60 (t, J=6.4 Hz, 1H), 7.29-7.24 (m, 3H), 7.19-7.11 (m, 3H), 4.75 (q, J=4.8 Hz, J2=8.0 Hz 1H), 2.67 (q, J1=7.3 Hz, J2=14.2 Hz 1H), 2.54-2.50 (m, 2H), 2.39-2.08 (m, 4H), 1.89-1.82 (m, 1H).

Workup

  1. additionwas added to the solution upon completion of the reaction
  2. washThe mixture was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe crude product was purified by preparative-HPLC (eluted with petroleum ether/EtOAc=5:1)

Sources & evidence

ORD record
ord-e27f6ccbdd4b405788728ca07ada3d2a
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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