Sodium borohydride → HCID 86745709, compound

HRID 1030854Notes

Reaction equation

HRID 1030854 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9]1\[CH2:10][C@@H:11]2[C@H:15]([CH2:16]\1)[C@@H:14]([CH2:17][CH2:18][C:19](=[O:26])[CH:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[C@H:13]([O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[CH2:12]2)([O:3][CH3:4])=[O:2].[BH4-].[Na+]>CO>[C:1]([CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9]1\[CH2:10][C@@H:11]2[C@H:15]([CH2:16]\1)[C@@H:14]([CH2:17][CH2:18][CH:19]([OH:26])[CH:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[C@H:13]([O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[CH2:12]2)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86745710HCID 86745710, compound

Product 1

HCID 86745709HCID 86745709, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,2R,3R,5S)-7(E)-(4-Carbomethoxybutylidene)-2-[4(RS)-fluoro-3-oxo-octyl]-3-tetrahydropyranyloxybicyclo[ 3.3.0]octane (11) (0.197 g) was dissolved in methanol, to which a sodium borohydride (0.017 g) was added at 0° C. The mixture was stirred for 30 minutes and treated as a usual work-up. A crude product obtained was chromatographed (hexane/ethyl acetate=3/1) to give (1S,2R,3R,5S)-7(E)-(4-carbomethoxybutylidene)-2-[4(RS)-fluoro-3(RS)-hydroxy-octyl]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (12). Yield: 0.185 g (93%)

Workup

  1. additionwas added at 0° C
  2. additiontreated as a usual work-up
  3. customA crude product obtained
  4. customwas chromatographed (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b91fdef5c8cd408faa65c623e3a4577a
Source dataset
uspto-grants-1992_04
Patent number
US05107014

Reaction notes

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