Sodium borohydride → HCID 22842860, compound

HRID 2293592Notes

Reaction equation

HRID 2293592 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 one (32) (5.48 g) in methanol was added sodium borohydride (0.800 g) at 0° C. and the resultant mixture was stirred for 10 minutes. The resultant mixture was worked up with the conventional procedure and the obtained crude product was subjected to column chromatography to give the titled compound (33). Yield: 5.46 g (99.5%).

Workup

  1. customthe obtained crude product

Sources & evidence

ORD record
ord-42f28eafc47b49cfb68b4458351de548
Source dataset
uspto-grants-1997_11
Patent number
US05686487

Reaction notes

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