Sodium borohydride → HCID 59132590, compound

HRID 1169855Notes

Reaction equation

HRID 1169855 reaction equation
[OH:1][C:2]1([C:12]2[N:16]([S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[C:15]([C:23]([O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[CH2:24])=[N:14][C:13]=2[CH3:36])[C@H:9]2[C@H:5]([O:6][C:7]([CH3:11])([CH3:10])[O:8]2)[CH2:4][O:3]1.[BH4-].[Na+]>C(O)C>[OH:1][C@@H:2]([C@H:9]1[C@@H:5]([CH2:4][OH:3])[O:6][C:7]([CH3:11])([CH3:10])[O:8]1)[C:12]1[N:16]([S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[C:15]([C:23]([O:25][Si:26]([CH:30]([CH3:31])[CH3:32])([CH:27]([CH3:29])[CH3:28])[CH:33]([CH3:34])[CH3:35])=[CH2:24])=[N:14][C:13]=1[CH3:36]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59132591HCID 59132591, compound

Product 1

HCID 59132590HCID 59132590, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. solution of 5-((3aR,6aR)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-N,N,4-trimethyl-2-(1-(triisopropylsilyloxy)vinyl)-1H-imidazole-1-sulfonamide (2.09 g, 3.83 mmol) in ethanol (70 ml) was added granular NaBH4 (1.4 g, 38.32 mmol) in a few portions. After 2 hours, the reaction was warmed to room temperature for 30 minutes, then concentrated. The residue was redissolved in water (40 ml) and ethyl acetate (40 ml). The biphasic mixture was stirred vigorously for 10 minutes, then the layers were separated. The aqueous layer was washed with ethyl acetate (2×40 ml) and the combined organics were washed with brine (30 ml), then dried over MgSO4 and concentrated. The crude foam was purified by flash chromatography over silica (5% methanol:dichloromethane eluent) to provide 5-((R)-hydroxy((4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-N,N,4-trimethyl-2-(1-(triisopropylsilyloxy)vinyl)-1H-imidazole-1-sulfonamide (1.88 g, 90% yield) as a 3:1 mixture of inseparable diasteromers at the benzylic position: M+1=547.4.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in water (40 ml)
  3. customthe layers were separated
  4. washThe aqueous layer was washed with ethyl acetate (2×40 ml)
  5. washthe combined organics were washed with brine (30 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude foam was purified by flash chromatography over silica (5% methanol:dichloromethane eluent)

Sources & evidence

ORD record
ord-71320da705b74bb3aa0c16ffdcf7e3ad
Source dataset
uspto-grants-2010_11
Patent number
US07825150B2

Reaction notes

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