Methanol → HCID 58944618, compound

HRID 222211Notes

Reaction equation

HRID 222211 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][CH:34]=[O:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO.[BH4-].[Na+]>>[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][CH2:34][OH:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydride2×HCID 58944646HCID 58944646, compound

Product 1

HCID 58944618HCID 58944618, compoundYield 45%

Conditions

Temperature
0 °C

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)acetaldehyde (0.164 g, 0.314 mmol) was dissolved in methanol (5.00 mL, 123 mmol) under an atmosphere of argon and cooled to 0° C. Sodium tetrahydroborate (0.0291 g, 0.754 mmol) was added and the reaction was stirred for 10 minutes. Additional sodium tetrahydroborate (0.0143 g, 0.377 mmol) was added, and the reaction mixture was stirred for another 30 minutes. The reaction was quenched with water, extracted with EtOAc, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of 0 to 100% EtOAc in methylene chloride, to afford the title compound (0.0694 g, 45%). LC/MS: Rt=1.65 min, ES+ 494 (FA standard).

Workup

  1. stirringthe reaction mixture was stirred for another 30 minutes
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of 0 to 100% EtOAc in methylene chloride

Sources & evidence

ORD record
ord-efb156193a6349e183d24d074f34712b
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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