Sodium borohydride → HCID 131717632, compound

HRID 373255Notes

Reaction equation

HRID 373255 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]=[CH:8][C:9]1[CH2:16][C@H:15]2[C@H:11]([CH2:12][C@@H:13]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[C@H:14]2/[CH:17]=[CH:18]/[C:19](=[O:27])[C:20]([F:26])([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:10]=1)=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]=[CH:8][C:9]1[CH2:16][C@H:15]2[C@H:11]([CH2:12][C@@H:13]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[C@H:14]2/[CH:17]=[CH:18]/[CH:19]([OH:27])[C:20]([F:26])([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131717633HCID 131717633, compound

Product 1

HCID 131717632HCID 131717632, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,5S,6S,7R)-3-[4-Methoxycarbonyl-1(EZ)-butenyl]-6-[4,4-difluoro-3-oxo-(E )-1-octenyl]-7-tetrahydropyranyloxy-bicyclo[3.3.0]oct-2-ene (16) (0.196 g) was dissolved in methanol. To the solution, sodium borohydride (0.015 g) was added at 0° C., and the mixture was stirred for 30 minutes. After a usual work-up (1S,5S,6S,7R)-3-[4-methoxycarbonyl-1(EZ)-butenyl]-6-[4, 4-difluoro-3-(RS)hydroxy-(E)-1--octenyl]-7-tetrahydropyranyloxy-bicyclo[3.3.0]oct-2-ene (17) was obtained as a colorless oily product. Yield: 0.184 g (93%)

Sources & evidence

ORD record
ord-fbd596d58e4d4ebc91f37bfbbf5a543b
Source dataset
uspto-grants-1992_11
Patent number
US05162370

Reaction notes

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