Methyl morpholine oxide → (1R,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentanecarbaldehyde

HRID 222204Notes

Reaction equation

HRID 222204 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][C@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:11][C@H:10]1[CH2:33][OH:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl>[Si:1]([O:8][C@H:9]1[CH2:13][C@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:11][C@H:10]1[CH:33]=[O:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58944620((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol

Product 1

HCID 58944601(1R,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentanecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol (257.0 mg, 0.0005369 mol) was dissolved in methylene chloride (10.0 mL) under argon. N-Methylmorpholine N-oxide (126 mg, 0.00107 mol), and 4 Å molecular sieves (250 mg, freshly flame dried) were then added and the mixture was stirred for 10 minutes at room temperature. Tetrapropylammonium perruthenateVII (18.9 mg, 0.0000537 mol) was then added, and the resulting dark green solution was stirred for 1 h at room temperature. The reaction mixture was filtered through a silica gel plug, eluting with DCM (20 mL), followed by 50% ethyl acetate in DCM (150 mL). The eluate was evaporated to provide the product as a clear light green oil. The residue was carried on to the next reaction without further purification.

Workup

  1. customdried)
  2. additionwere then added
  3. additionTetrapropylammonium perruthenateVII (18.9 mg, 0.0000537 mol) was then added
  4. stirringthe resulting dark green solution was stirred for 1 h at room temperature
  5. filtrationThe reaction mixture was filtered through a silica gel plug
  6. washeluting with DCM (20 mL)
  7. customThe eluate was evaporated

Sources & evidence

ORD record
ord-7865639e34184e43a1b09a7daf69537b
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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