Sodium borohydride → Ammonium Hydroxide

HRID 1890701Notes

Reaction equation

HRID 1890701 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:24][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[CH:18][C:17]([CH:22]=[O:23])=[CH:16]3.[BH4-].[Na+]>CO.C(Cl)Cl>[NH4+:6].[OH-:1].[OH:23][CH2:22][C:17]1[CH:18]=[N:19][C:20]2[C:15]([CH:16]=1)=[CH:14][C:13]1[CH2:24][C@:3]3([CH2:11][C:12]=1[CH:21]=2)[C:4]1[C:5](=[N:6][CH:7]=[CH:8][CH:9]=1)[NH:10][C:2]3=[O:1]

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 59594304HCID 59594304, compound2×

Product 2

HCID 14923Ammonium HydroxideHCID 58550612(3′S)-6,8-Dihydro-3-(hydroxymethyl)spiro[7H-cyclopenta[g]quinoline-7,3′-[3H]pyrrolo[2,3-b]pyridin]-2′(1′H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-3-carbaldehyde (1.79 g, 5.68 mmol, described in Intermediate 1) in a mixture of MeOH (30 mL) and CH2Cl2 (10 mL) was added sodium borohydride (322 mg, 8.52 mmol). The resulting mixture was stirred at ambient temperature for 48 h, with additional sodium borohydride (322 mg, 8.52 mmol) added at 16 and 20 h. The solvents were removed in vacuo and the residue was partitioned between saturated aqueous NaHCO3 (100 mL) and CH2Cl2 (100 mL). The aqueous layer was extracted further with CH2Cl2 (2×100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 95:5:1, to give the title compound. MS: m/z=318 (M+1).

Workup

  1. additionadded at 16 and 20 h
  2. customThe solvents were removed in vacuo
  3. customthe residue was partitioned between saturated aqueous NaHCO3 (100 mL) and CH2Cl2 (100 mL)
  4. extractionThe aqueous layer was extracted further with CH2Cl2 (2×100 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-54fce952ab33439ebb584be363d3dd40
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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