Ethanol → HCID 178455357, compound

HRID 2095713Notes

Reaction equation

HRID 2095713 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH:20]=[O:21])=[C:18]([I:22])[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCO.[BH4-].[Na+]>>[Si:1]([O:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([N:15]2[C:19]([CH2:20][OH:21])=[C:18]([I:22])[CH:17]=[N:16]2)[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 178455356HCID 178455356, compound

Product 1

HCID 178455357HCID 178455357, compound

Procedure

To a solution of 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-1H-pyrazole-5-carbaldehyde (50.0 mg, 0.115 mmol) in EtOH (3 mL, 50 mmol) was added sodium borohydride (6.53 mg, 0.173 mmol) at rt, and the mixture was stirred for 10 min. The solution was dry-loaded onto silica gel and purified via column chromatography, eluting with 3-5% EtOH/heptane. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z=437.08 (100) [MH+]. HPLC: tR=1.88 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. custompurified via column chromatography
  2. washeluting with 3-5% EtOH/heptane
  3. additionThe fractions containing the pure product
  4. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-c600ebb8b7fe448fa335dcfe8378b460
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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