Triphenylphosphine → HCID 86629375, compound

HRID 1093209Notes

Reaction equation

HRID 1093209 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:15][C:16]1[N:21]=[C:20]2[NH:22][N:23]=[CH:24][C:19]2=[C:18]([N:25]2[CH2:31][CH:30]3[O:32][CH:27]([CH2:28][CH2:29]3)[CH2:26]2)[N:17]=1.[O:33]1[C:37]2([CH2:42][CH2:41][CH:40](O)[CH2:39][CH2:38]2)[CH2:36][CH2:35][CH2:34]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:15][C:16]1[N:21]=[C:20]2[N:22]([CH:40]3[CH2:41][CH2:42][C:37]4([O:33][CH2:34][CH2:35][CH2:36]4)[CH2:38][CH2:39]3)[N:23]=[CH:24][C:19]2=[C:18]([N:25]2[CH2:31][CH:30]3[O:32][CH:27]([CH2:28][CH2:29]3)[CH2:26]2)[N:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 201118843-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octaneHCID 2014413887151-62-0

Product 1

HCID 86629375HCID 86629375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (2.6 mL, 13 mmol) was added in drops to a mixture of 3-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (2.6 g, 10 mmol), 1-oxaspiro[4.5]decan-8-ol (U.S. Pat. No. 4,438,130, Mar. 20, 1984, 1.6 g, 11 mmol), and triphenylphosphine (2.9 g, 11 mmol) in tetrahydrofuran (80 mL). After stirring at room temperature, the mixture was purified by reverse phase high performance liquid chromatography on a Phenomenex Prodigy 21 mm×250 mm column, running a gradient elution of 15% acetonitrile/85% of 0.1% aqueous trifluoroacetic acid to 100% acetonitrile to provide two separable diastereomers of 3-(6-chloro-1-(1-oxaspiro[4.5]decan-8-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. MS (ES+): 404.2 (M+H)+

Workup

  1. customthe mixture was purified by reverse phase high performance liquid chromatography on a Phenomenex Prodigy 21 mm×250 mm column
  2. washa gradient elution of 15% acetonitrile/85% of 0.1% aqueous trifluoroacetic acid to 100% acetonitrile

Sources & evidence

ORD record
ord-c9ca63c87df7402a9465c129f8c84e12
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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