Sodium triacetoxyborohydride → HCID 69810790, compound

HRID 529122Notes

Reaction equation

HRID 529122 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[N:9]([C:24]3[C:25]4[C@H:32]([CH3:33])[CH2:31][CH2:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:10][C:11]3([CH2:16][CH2:15][N:14]([C:17](OC(C)(C)C)=O)[CH2:13][CH2:12]3)[C:4]=12.[BH-](O[C:44]([CH3:46])=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.ClCCCl.C(Cl)Cl>[CH2:17]([N:14]1[CH2:13][CH2:12][C:11]2([C:4]3[C:5](=[CH:6][CH:7]=[CH:8][C:3]=3[CH2:2][NH:1][CH:46]3[CH2:44][CH2:12][CH2:11][CH2:10]3)[N:9]([C:24]3[C:25]4[C@H:32]([CH3:33])[CH2:31][CH2:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:10]2)[CH2:16][CH2:15]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 69810509HCID 69810509, compound

Product 1

HCID 69810790HCID 69810790, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopentone (0.036 mL, 0.40 mmol) in THF (0.15 mL) was added to a stirred solution of (R)-tert-butyl 4-(aminomethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (30 mg, 0.067 mmol) in DCE (0.6 mL). The reaction was allowed to stir at room temperature for 15 minutes, at which point Na(OAc)3BH was added, and the reaction allowed to stir at room temperature for 2 hours. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography (DCM:MeOH, 20:1) to give (R)—N-((1′-benzyl-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)cyclopentanamine (34 mg, 98%) as an oil. LCMS (APCI+) m/z 518 [M+H]+; Rt=2.91 min.

Workup

  1. additionwas added
  2. washwashed with saturated aqueous NaHCO3 solution and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (DCM:MeOH, 20:1)

Sources & evidence

ORD record
ord-3f9822df4a2848f79d4ea231d57815ad
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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