Triphenylphosphine → HCID 86706486, compound

HRID 919651Notes

Reaction equation

HRID 919651 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1.O[CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH2:10][C:9]1[N:1]=[CH:2][N:3]=[C:4]2[C:8]=1[N:7]=[CH:6][N:5]2[CH:16]1[CH2:17][CH2:12][CH2:13][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5456991-Boc-3-hydroxypiperidineHCID 5363146Diisopropyl azodicarboxylateHCID 178508693HCID 178508693, compound

Product 1

HCID 86706486HCID 86706486, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9H-purin-6-amine (945 mg, 7 mmol, 1.0 eq) in THF (1 mL) was added tert-butyl 3-hydroxypiperidine-1-carboxylate (2.996 g, 14 mmol, 2.0 eq) and PPh3 (3.67 g, 14 mmol, 2.0 eq). After stirring for the solution for 15 min, DIAD (2.83 g, 14 mmol, 2.0 eq) was added the reaction was continued to be stirred rt for 1 h. The solvent was removed in vacuo and the residue was purified on a silica gel column (PE/EA=5:1) to afford the title compound as a yellow solid (245 mg, yield 11%). 1H NMR (400 MHz, CD3OD) δ: 8.44 (s, 1H), 8.42 (s, 1H), 5.04-4.98 (m, 1H), 3.77-3.73 (m, 1H), 3.68-3.62 (m, 1H), 3.52-3.48 (m, 1H), 3.18-3.11 (m, 1H), 2.45-2.32 (m, 2H), 2.22-2.17 (m, 1H), 2.05-1.97 (m, 1H), 1.49 (s, 9H). ESI-MS: 319.1 (M+H+).

Workup

  1. stirringto be stirred rt for 1 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified on a silica gel column (PE/EA=5:1)

Sources & evidence

ORD record
ord-4bd284e5d5be40af9d4b7efbeb675798
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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