Sodium borohydride → HCID 22842860, compound

HRID 373596Notes

Reaction equation

HRID 373596 reaction equation
[F:1][C:2]([F:27])([C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][CH2:5][C@H:6]1[C@H:13]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH2:12][C@H:11]2[C@@H:7]1[CH2:8][C:9](=[O:21])[O:10]2.[BH4-].[Na+]>CO>[F:27][C:2]([F:1])([CH:22]([OH:26])[CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][CH2:5][C@H:6]1[C@H:13]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH2:12][C@H:11]2[C@@H:7]1[CH2:8][C:9](=[O:21])[O:10]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22842859HCID 22842859, compound

Product 1

HCID 22842860HCID 22842860, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S,5R,6R,7R)-6-(4,4-difluoro-5-oxooctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3- one (32) (5.48 g) in methanol was added sodium borohydride (0.800 g) at 0° C. and the resulting mixture was stirred for 10 minutes. The reaction mixture was treated in the conventional manner and the obtained crude product was subjected to column chromatography to give the title compound (33).

Workup

  1. additionThe reaction mixture was treated in the conventional manner
  2. customthe obtained crude product

Sources & evidence

ORD record
ord-5d81f82859624def92e45ff105b86a92
Source dataset
uspto-grants-1992_11
Patent number
US05164415

Reaction notes

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