HCID 67540338, compound → HCID 67539623, compound

HRID 1880210Notes

Reaction equation

HRID 1880210 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]3)=[O:15])[CH2:11][CH:10]2[C:26]#[N:27])[CH:5]=[CH:6][C:7]=1[Cl:8]>O1CCCC1>[NH2:27][CH2:26][CH:10]1[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:13][N:12]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:23])=[O:24])[CH2:18][CH2:17]2)=[O:15])[CH2:11]1

Participants

3

Reactant 1

HCID 67540338HCID 67540338, compound

Product 1

HCID 67539623HCID 67539623, compoundYield 569.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (3SR,4RS)-4-(3,4-Dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidine-3-carbonitrile (0.1 g, 0.23 mmol) in tetrahydrofuran (1.0 mL) at 0° C. was added BH3 in tetrahydrofuran (0.55 mL, 0.55 mmol). After 2 hours of stirring at ambient temperature the reaction mixture was quenched with MeOH and the volatiles were removed under vacuo. The residue was taken up in H2O, extracted with EtOAc and the combined organic phases were dried over Na2SO4. Flash chromatography (SiO2, EtOAc, then CH2Cl2/MeOH 19:1) yielded the title product (0.57 g, 56%) as a colorless oil. ES-MS m/e: 436.1 (M+H+).

Workup

  1. customwas quenched with MeOH
  2. customthe volatiles were removed under vacuo
  3. extractionextracted with EtOAc
  4. dry with materialthe combined organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-840313ab6f8d418ea5624c162c0367a2
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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