Sodium borohydride → HCID 131717630, compound

HRID 373253Notes

Reaction equation

HRID 373253 reaction equation
C12CCCC1CC=C2.[CH3:9][O:10][C:11]([CH2:13][CH2:14][CH:15]=[CH:16][C:17]1[CH2:24][C@H:23]2[C@H:19]([CH2:20][C@@H:21]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[C@H:22]2/[CH:25]=[CH:26]/[C:27](=[O:34])[CH:28]([F:33])[CH2:29][CH2:30][CH2:31][CH3:32])[CH:18]=1)=[O:12].[BH4-].[Na+]>CO>[CH3:9][O:10][C:11]([CH2:13][CH2:14][CH:15]=[CH:16][C:17]1[CH2:24][C@H:23]2[C@H:19]([CH2:20][C@@H:21]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[C@H:22]2/[CH:25]=[CH:26]/[CH:27]([OH:34])[CH:28]([F:33])[CH2:29][CH2:30][CH2:31][CH3:32])[CH:18]=1)=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131717631HCID 131717631, compound

Product 1

HCID 131717630HCID 131717630, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,5S,6S,7R)-3-[4-Methoxycarbonyl-1(EZ)-butenyl]-6-[4(RS)-fluoro-3-oxo-(E )-1-octenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene bicyclo[3.3.0]oct-2-ene (5) (0.088g) was dissolved in methanol. Into the solution, sodium borohydride (0.008 g) was added at 0° C. and the mixture was stirred for 30 minutes. The reaction mixture was treated by a usual manner to give (1S,5S,6S,7R)-3-[4-methoxycarbonyl-1(EZ)-butenyl]-6-[4(RS)-fluoro-3(R S)-hydroxy-(E)-1-octenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (5") as a colorless oily product. Yield: 0.089 g

Workup

  1. additionThe reaction mixture was treated by a usual manner

Sources & evidence

ORD record
ord-faaeaad4fd744863ac05942bca211fa3
Source dataset
uspto-grants-1992_11
Patent number
US05162370

Reaction notes

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