Lithium aluminum hydride → N-[((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)methyl]-N-methylsulfamide

HRID 222209Notes

Reaction equation

HRID 222209 reaction equation
C(O[C:6](=O)[N:7]([S:41]([NH2:44])(=[O:43])=[O:42])[CH2:8][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[O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])(C)(C)C.[AlH4-].[Li+]>O1CCCC1>[Si:34]([O:33][C@H:10]1[CH2:11][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)[CH2:13][C@H:9]1[CH2:8][N:7]([CH3:6])[S:41]([NH2:44])(=[O:42])=[O:43])([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:35])[CH3:36]

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 58944590tert-butyl (aminosulfonyl)[((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)methyl]carbamate

Product 1

HCID 58944658N-[((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)methyl]-N-methylsulfamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl(aminosulfonyl)[((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)-methyl]carbamate (108 mg, 0.000164 mol) was dissolved in tetrahydrofuran (2.0 mL) under an atmosphere of nitrogen. Lithium tetrahydroaluminate (12.5 mg, 0.000329 mol) was added and the mixture heated at 50° C. for 80 minutes. The reaction was then cooled, quenched with water and acidified to ˜pH 6 with 1M HCl. This mixture was then extracted with ethyl acetate, the separated organic phase was evaporated, and the residue was purified by silica gel chromatography, eluting with 10 to 100% ethyl acetate in hexanes, to yield the product, 25 mg (27%). LC/MS: Rt=2.34 min, ES+ 571 (AA standard).

Workup

  1. temperatureThe reaction was then cooled
  2. customquenched with water
  3. extractionThis mixture was then extracted with ethyl acetate
  4. customthe separated organic phase was evaporated
  5. customthe residue was purified by silica gel chromatography
  6. washeluting with 10 to 100% ethyl acetate in hexanes
  7. customto yield the product, 25 mg (27%)

Sources & evidence

ORD record
ord-79fed75d5d624056ba91a5ec4713f0ce
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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