Borane → HCID 67173148, compound

HRID 656407Notes

Reaction equation

HRID 656407 reaction equation
[N+:1]([C:4]1[CH:21]=[C:20]2[C:7]([CH2:8][C@:9]3([CH2:19]2)[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]3=[O:18])=[CH:6][C:5]=1[CH2:22][C:23](O)=[O:24])([O-:3])=[O:2].B>C1COCC1>[OH:24][CH2:23][CH2:22][C:5]1[CH:6]=[C:7]2[C:20](=[CH:21][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:19][C@:9]1([C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]1=[O:18])[CH2:8]2

Participants

4

Reactant 2

HCID 6331BoraneHCID 67174106HCID 67174106, compound

Product 1

HCID 67173148HCID 67173148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of [(2S)-6-nitro-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-yl]acetic acid from Step D (753 mg, 2.22 mmol) in THF (15 mL), at −78° C., was added borane (1 M in THF; 9.1 mL, 9.1 mmol) dropwise. After 5 min, the mixture was warmed to 0° C. and stirring was continued at this temperature for 3 h. The reaction was quenched carefully with 1 N HCl and stirring was continued at ambient temperature. The mixture was adjusted to pH 8 with saturated aqueous NaHCO3 and extracted with EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 80:20, to give the title compound. MS: m/z=326 (M+1).

Workup

  1. waitwas continued at this temperature for 3 h
  2. customThe reaction was quenched carefully with 1 N HCl
  3. stirringstirring
  4. customwas continued at ambient temperature
  5. extractionextracted with EtOAc (2×100 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-dbf413f73c124d4797b1475d29f265fe
Source dataset
uspto-grants-2011_12
Patent number
US08071771B2

Reaction notes

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