Cyclopentanone → HCID 68758818, compound

HRID 529158Notes

Reaction equation

HRID 529158 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][NH2:23])[N:15]([C:24]3[C:25]4[CH:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][CH2:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]1(=O)[CH2:40][CH2:39][CH2:38][CH2:37]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][NH:23][CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[N:15]([C:24]3[C:25]4[CH:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][CH2:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8452Cyclopentanone2×HCID 5049666Sodium triacetoxyborohydride2×HCID 68760847HCID 68760847, compound

Product 1

HCID 68758818HCID 68758818, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirring solution of (1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methanamine (0.250 g, 0.433 mmol) in DCE (3 mL) was treated with cyclopentanone (0.192 mL, 2.17 mmol). The reaction was allowed to stir for 20 minutes, followed by the addition of NaBH(OAc)3 (0.184 g, 0.867 mmol). The reaction was stirred at room temperature overnight. An additional 2.5 equivalents of cyclopentanone and 1.0 eq of NaBH(OAc)3 were added to the reaction and stirred an additional 2 hours. The reaction was quenched by the addition of saturated NaHCO3 and diluted with DCM. The combined organics were washed with brine, dried Na2SO4, filtered, and concentrated under reduced pressure to yield N-((1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)cyclopentanamine (0.211 g, 91%), which was used without further purification. LCMS (APCI+) m/z 536.4 [M+H]+; Rt=3.61 min.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. stirringstirred an additional 2 hours
  3. customThe reaction was quenched by the addition of saturated NaHCO3
  4. additiondiluted with DCM
  5. washThe combined organics were washed with brine, dried Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-009923bc849a4f5ba93e8dd0bc464273
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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