Acetone → HCID 68764711, compound

HRID 529132Notes

Reaction equation

HRID 529132 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]2[N:23]([C:37]3[C:38]4[C@H:45]([CH3:46])[CH2:44][C@@H:43]([OH:47])[C:39]=4[N:40]=[CH:41][N:42]=3)[CH2:24][C@@:25]3([CH2:29][CH2:28][N:27]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:26]3)[C:18]=12.[CH3:48][C:49]([CH3:51])=O>ClCCCl.C(Cl)Cl>[CH2:30]([N:27]1[CH2:28][CH2:29][C@:25]2([C:18]3[C:19](=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][NH:15][CH:49]([CH3:51])[CH3:48])[N:23]([C:37]3[C:38]4[C@H:45]([CH3:46])[CH2:44][C@@H:43]([OH:47])[C:39]=4[N:40]=[CH:41][N:42]=3)[CH2:24]2)[CH2:26]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 69810649HCID 69810649, compound

Product 1

HCID 68764711HCID 68764711, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

NaBH(OAc)3 (57.6 mg, 0.272 mmol) was added to a solution of (5R,7R)-4-((S)-4-(aminomethyl)-1′-benzylspiro[indoline-3,3′-pyrrolidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol (40 mg, 0.091 mmol), acetone (52.6 mg, 0.906 mmol) in DCE (1.0 mL), and the resulting solution was stirred at ambient temperature for 8 hours. The reaction mixture was diluted with DCM and washed with 25% NaOH. The aqueous layer was separated and extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to give (5R,7R)-4-((S)-1′-benzyl-4-((isopropylamino)methyl)spiro[indoline-3,3′-pyrrolidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol (40.0 mg, 0.083 mmol, 91%). LCMS (APCI+) M+H+ 484 (100%); Rt=2.64 min.

Workup

  1. washwashed with 25% NaOH
  2. customThe aqueous layer was separated
  3. extractionextracted with DCM (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e5295b1ada7413882195be4ff16ff67
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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