Diisopropylethylamine → HCID 58550625, compound

HRID 1890714Notes

Reaction equation

HRID 1890714 reaction equation
Cl.Cl.C[CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1([NH:12][CH2:13][CH2:14][C@H:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([OH:11])=[O:10].[O:23]=[C:24]1[NH:32][C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C@:25]21[CH2:46][C:35]1[CH:36]=[C:37]3[C:42](=[CH:43][C:34]=1[CH2:33]2)[N:41]=[CH:40][C:39]([CH:44]=O)=[CH:38]3.[CH3:47]CN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl>[O:23]=[C:24]1[NH:32][C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C@:25]21[CH2:46][C:35]1[CH:36]=[C:37]3[C:42](=[CH:43][C:34]=1[CH2:33]2)[N:41]=[CH:40][C:39]([CH2:44][NH:22][C@H:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:14][CH2:13][NH:12][C:5]1([C:9]([O:11][CH3:47])=[O:10])[CH2:4][CH2:8][CH2:7][CH2:6]1)=[CH:38]3

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59594304HCID 59594304, compound2×HCID 67996087HCID 67996087, compound

Product 1

HCID 58550625HCID 58550625, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of methyl-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate dihydrochloride (222 mg, 0.634 mmol, prepared according to U.S. Patent Application Publication No. US 2007/0265225) and (7S)-2′-oxo-1′,2′, 6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-3-carbaldehyde (200 mg, 0.634 mmol, Intermediate 1) in chloroform (16 mL) was added Hunig's base (0.222 mL, 1.27 mmol). One hour later, sodium triacetoxyborohydride (403 mg, 1.90 mmol) was added. Two hours later, the reaction was quenched by the addition of saturated sodium bicarbonate (3 mL) and the reaction was allowed to stir for an additional 30 minutes. This mixture was further diluted with water (10 mL) and chloroform (40 mL). The aqueous layer was separated and extracted once with chloroform (30 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue. This residue was applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH (10% conc. NH4OH)—99:1 to 90:10. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=576 (M+1).

Workup

  1. customTwo hours later, the reaction was quenched by the addition of saturated sodium bicarbonate (3 mL)
  2. additionThis mixture was further diluted with water (10 mL) and chloroform (40 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted once with chloroform (30 mL)
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a residue
  9. customThis residue was applied to a silica gel column for purification
  10. washeluting with a gradient of CH2Cl2
  11. additionClean product-containing fractions
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-347ae3b094834b4db50870cdf369ca0e
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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