Water → 6-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-ol

HRID 913059Notes

Reaction equation

HRID 913059 reaction equation
[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[N:16]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[N:19]=2)=[O:14])[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].[BH4-].[Na+].O>CCO>[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]2[N:16]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:36])([CH3:37])[CH3:35])[CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[N:19]=2)[OH:14])[O:4][CH2:5][CH2:6][O:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 673819946-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-one

Product 1

HCID 673820876-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the ketone F1 in EtOH (0.04 M solution) at 0° C. was added NaBH4 (2.0 eq.) and the mixture was stirred for 1 hr. Water was slowly added and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried (MgSO4) and solvents were removed under reduced pressure. The crude product was used without purification in the next step. MS (ES) C30H44N2O4Si requires: 525, found: 526 (M+H)+.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (MgSO4) and solvents
  3. customwere removed under reduced pressure
  4. customThe crude product was used without purification in the next step

Sources & evidence

ORD record
ord-a5cd1468753140538d775661d14cb41c
Source dataset
uspto-grants-2011_09
Patent number
US08026265B2

Reaction notes

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